{"id":571,"date":"2019-04-16T19:29:35","date_gmt":"2019-04-16T19:29:35","guid":{"rendered":"https:\/\/sites.uni.edu\/chin\/?p=571"},"modified":"2019-04-16T19:29:37","modified_gmt":"2019-04-16T19:29:37","slug":"what-an-ordeal","status":"publish","type":"post","link":"https:\/\/sites.uni.edu\/chin\/2019\/04\/16\/what-an-ordeal\/","title":{"rendered":"What an ordeal"},"content":{"rendered":"\n<p>Trying to make some 3-triethylsilylpyridine to use as a standard for our reactions. Reaction seems straight forward enough.<\/p>\n\n\n\n<figure class=\"wp-block-image\"><img loading=\"lazy\" decoding=\"async\" width=\"671\" height=\"424\" src=\"https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image.png\" alt=\"\" class=\"wp-image-572\" srcset=\"https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image.png 671w, https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-300x190.png 300w\" sizes=\"auto, (max-width: 671px) 100vw, 671px\" \/><figcaption>From Glorius and co-workers, Angew. Chemie, 2018, 8297. They used Me3SiCl instead and a bromopyridine instead of an iodo. <\/figcaption><\/figure>\n\n\n\n<p>Get dry ice from local Hy-Vee (the one where Kurt Warner used to work). Cool stuff down. Looks like orange crush after the silane addition. <\/p>\n\n\n\n<figure class=\"wp-block-image\"><img loading=\"lazy\" decoding=\"async\" width=\"576\" height=\"1024\" src=\"https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-1-576x1024.png\" alt=\"\" class=\"wp-image-573\" srcset=\"https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-1-576x1024.png 576w, https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-1-169x300.png 169w, https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-1-768x1366.png 768w, https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-1.png 1920w\" sizes=\"auto, (max-width: 576px) 100vw, 576px\" \/><figcaption>To slurp or not to slurp?<\/figcaption><\/figure>\n\n\n\n<p>Crude NMR spectrum looked fairly messy. <\/p>\n\n\n\n<figure class=\"wp-block-image\"><img loading=\"lazy\" decoding=\"async\" width=\"852\" height=\"524\" src=\"https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-2.png\" alt=\"\" class=\"wp-image-574\" srcset=\"https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-2.png 852w, https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-2-300x185.png 300w, https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-2-768x472.png 768w\" sizes=\"auto, (max-width: 852px) 100vw, 852px\" \/><figcaption>Distillation time?<\/figcaption><\/figure>\n\n\n\n<p>Tried a distillation to clean it up. <\/p>\n\n\n\n<figure class=\"wp-block-image\"><img loading=\"lazy\" decoding=\"async\" width=\"576\" height=\"1024\" src=\"https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-3-576x1024.png\" alt=\"\" class=\"wp-image-575\" srcset=\"https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-3-576x1024.png 576w, https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-3-169x300.png 169w, https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-3-768x1366.png 768w, https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-3.png 1920w\" sizes=\"auto, (max-width: 576px) 100vw, 576px\" \/><figcaption>Yup. Pipe cleaner on a spatula dipped in liq. N2 to cool the top<\/figcaption><\/figure>\n\n\n\n<p>Not the best. Still a bunch of silanol. <\/p>\n\n\n\n<p>Another distillation. A real on  this time<\/p>\n\n\n\n<figure class=\"wp-block-image\"><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"576\" src=\"https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-4-1024x576.png\" alt=\"\" class=\"wp-image-576\" srcset=\"https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-4-1024x576.png 1024w, https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-4-300x169.png 300w, https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-4-768x432.png 768w\" sizes=\"auto, (max-width: 1024px) 100vw, 1024px\" \/><\/figure>\n\n\n\n<p>NMR spectrum says cleanish, the GCMS says otherwise<\/p>\n\n\n\n<figure class=\"wp-block-image\"><img loading=\"lazy\" decoding=\"async\" width=\"849\" height=\"515\" src=\"https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-5.png\" alt=\"\" class=\"wp-image-577\" srcset=\"https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-5.png 849w, https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-5-300x182.png 300w, https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-5-768x466.png 768w\" sizes=\"auto, (max-width: 849px) 100vw, 849px\" \/><figcaption><br><\/figcaption><\/figure>\n\n\n\n<figure class=\"wp-block-image\"><img loading=\"lazy\" decoding=\"async\" width=\"561\" height=\"612\" src=\"https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-6.png\" alt=\"\" class=\"wp-image-578\" srcset=\"https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-6.png 561w, https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-6-275x300.png 275w\" sizes=\"auto, (max-width: 561px) 100vw, 561px\" \/><\/figure>\n\n\n\n<p>Had to dig deep to clean this thing up. The old prep TLC. The best way to do chromatography. It is like the Hawaiian pizza of chromatography. The absolute best. <\/p>\n\n\n\n<figure class=\"wp-block-image\"><img loading=\"lazy\" decoding=\"async\" width=\"576\" height=\"1024\" src=\"https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-7-576x1024.png\" alt=\"\" class=\"wp-image-579\" srcset=\"https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-7-576x1024.png 576w, https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-7-169x300.png 169w, https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-7-768x1366.png 768w, https:\/\/sites.uni.edu\/chin\/wp-content\/uploads\/2019\/04\/image-7.png 1920w\" sizes=\"auto, (max-width: 576px) 100vw, 576px\" \/><\/figure>\n\n\n\n<p>Only 66.6 mgs of product. But at least it was clean. And the final mass seems like a sign that I should not pursue this any further. <\/p>\n","protected":false},"excerpt":{"rendered":"<p>Trying to make some 3-triethylsilylpyridine to use as a standard for our reactions. Reaction seems straight forward enough. Get dry ice from local Hy-Vee (the one where Kurt Warner used to work). Cool stuff down. Looks like orange crush after the silane addition. Crude NMR spectrum looked fairly messy. Tried a distillation to clean it [&hellip;]<\/p>\n","protected":false},"author":2,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"ocean_post_layout":"","ocean_both_sidebars_style":"","ocean_both_sidebars_content_width":0,"ocean_both_sidebars_sidebars_width":0,"ocean_sidebar":"0","ocean_second_sidebar":"0","ocean_disable_margins":"enable","ocean_add_body_class":"","ocean_shortcode_before_top_bar":"","ocean_shortcode_after_top_bar":"","ocean_shortcode_before_header":"","ocean_shortcode_after_header":"","ocean_has_shortcode":"","ocean_shortcode_after_title":"","ocean_shortcode_before_footer_widgets":"","ocean_shortcode_after_footer_widgets":"","ocean_shortcode_before_footer_bottom":"","ocean_shortcode_after_footer_bottom":"","ocean_display_top_bar":"default","ocean_display_header":"default","ocean_header_style":"","ocean_center_header_left_menu":"0","ocean_custom_header_template":"0","ocean_custom_logo":0,"ocean_custom_retina_logo":0,"ocean_custom_logo_max_width":0,"ocean_custom_logo_tablet_max_width":0,"ocean_custom_logo_mobile_max_width":0,"ocean_custom_logo_max_height":0,"ocean_custom_logo_tablet_max_height":0,"ocean_custom_logo_mobile_max_height":0,"ocean_header_custom_menu":"0","ocean_menu_typo_font_family":"0","ocean_menu_typo_font_subset":"","ocean_menu_typo_font_size":0,"ocean_menu_typo_font_size_tablet":0,"ocean_menu_typo_font_size_mobile":0,"ocean_menu_typo_font_size_unit":"px","ocean_menu_typo_font_weight":"","ocean_menu_typo_font_weight_tablet":"","ocean_menu_typo_font_weight_mobile":"","ocean_menu_typo_transform":"","ocean_menu_typo_transform_tablet":"","ocean_menu_typo_transform_mobile":"","ocean_menu_typo_line_height":0,"ocean_menu_typo_line_height_tablet":0,"ocean_menu_typo_line_height_mobile":0,"ocean_menu_typo_line_height_unit":"","ocean_menu_typo_spacing":0,"ocean_menu_typo_spacing_tablet":0,"ocean_menu_typo_spacing_mobile":0,"ocean_menu_typo_spacing_unit":"","ocean_menu_link_color":"","ocean_menu_link_color_hover":"","ocean_menu_link_color_active":"","ocean_menu_link_background":"","ocean_menu_link_hover_background":"","ocean_menu_link_active_background":"","ocean_menu_social_links_bg":"","ocean_menu_social_hover_links_bg":"","ocean_menu_social_links_color":"","ocean_menu_social_hover_links_color":"","ocean_disable_title":"default","ocean_disable_heading":"default","ocean_post_title":"","ocean_post_subheading":"","ocean_post_title_style":"","ocean_post_title_background_color":"","ocean_post_title_background":0,"ocean_post_title_bg_image_position":"","ocean_post_title_bg_image_attachment":"","ocean_post_title_bg_image_repeat":"","ocean_post_title_bg_image_size":"","ocean_post_title_height":0,"ocean_post_title_bg_overlay":0.5,"ocean_post_title_bg_overlay_color":"","ocean_disable_breadcrumbs":"default","ocean_breadcrumbs_color":"","ocean_breadcrumbs_separator_color":"","ocean_breadcrumbs_links_color":"","ocean_breadcrumbs_links_hover_color":"","ocean_display_footer_widgets":"default","ocean_display_footer_bottom":"default","ocean_custom_footer_template":"0","ocean_post_oembed":"","ocean_post_self_hosted_media":"","ocean_post_video_embed":"","ocean_link_format":"","ocean_link_format_target":"self","ocean_quote_format":"","ocean_quote_format_link":"post","ocean_gallery_link_images":"off","ocean_gallery_id":[],"footnotes":""},"categories":[1],"tags":[],"class_list":["post-571","post","type-post","status-publish","format-standard","hentry","category-uncategorized","entry"],"_links":{"self":[{"href":"https:\/\/sites.uni.edu\/chin\/wp-json\/wp\/v2\/posts\/571","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/sites.uni.edu\/chin\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/sites.uni.edu\/chin\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/sites.uni.edu\/chin\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/sites.uni.edu\/chin\/wp-json\/wp\/v2\/comments?post=571"}],"version-history":[{"count":2,"href":"https:\/\/sites.uni.edu\/chin\/wp-json\/wp\/v2\/posts\/571\/revisions"}],"predecessor-version":[{"id":581,"href":"https:\/\/sites.uni.edu\/chin\/wp-json\/wp\/v2\/posts\/571\/revisions\/581"}],"wp:attachment":[{"href":"https:\/\/sites.uni.edu\/chin\/wp-json\/wp\/v2\/media?parent=571"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/sites.uni.edu\/chin\/wp-json\/wp\/v2\/categories?post=571"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/sites.uni.edu\/chin\/wp-json\/wp\/v2\/tags?post=571"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}