化学工作者的日常

交流化学知识提高有机水平了解一只有机喵的日常生活与工作

投稿

订阅

订阅数

获赞数

154

阅读数

59.7万

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合成戊酰（R）-(-)苄基Evans

松田诚一

NKU

在下松田诚一2020/05/15 14:33:39化学工作者的日常

中文摘要

Evans辅基可以用于手性合成，在不对称合成中应用较为广泛。此次合成手性反应的前体戊酰（R）-(-)苄基Evans

关键词

有机合成合成戊酰（R）-(-)苄基Evans手性反应的前体丁基锂

Evans辅基可以用于手性合成，在不对称合成中应用较为广泛。

此次合成手性反应的前体戊酰（R）-(-)苄基Evans

后续操作目前无法透露，过一阵子也许可以陆续上传

【纯粹是保密而已（笑）】

（绘图软件：chemdraw）

称取Evans辅剂至于四颈瓶组装好装置，一口装置温度计一口装三通阀中间装恒压漏斗最后一口翻口塞封闭用封口膜包裹密封用于取样监测反映

所有设备从烘箱中取出，设备使用之前用热风枪或电吹风热风除水

气球充入氩气并将装置气体置换三次使之氩气保护

【注：此处图片丢失具体操作方法详见鄙人上篇文章

用双尖针引入溶剂THF

将冷阱预冷至-80℃

将反应器至于其中搅拌冷却，待体系温度降至-78度以下后向恒压漏斗中加入正丁基锂

氩气保护下用长针头吸取

吸到指定体积后针头离开液面吹打几次排净针头内的锂试剂

将丁基锂注入恒压漏斗中，小心缓慢滴加

此步攫氢放热较为剧烈，必须缓慢滴加保证温度在-70℃以下

加入后颜色变为黄色-78℃搅拌1h颜色变为黄褐色

吸取少量THF冲洗恒压漏斗洗去，壁上残留的丁基锂

避免与加入的酰氯反应发烟

将戊酰氯加入恒压滴液漏斗

注：臭死了一股大便混合香港脚的味道还有酰氯的刺激性酸味（笑）

此步氮负离子进攻酰氯羰基，略有放热

小心缓慢滴加

加入后体系颜色变淡，从黄褐色变为淡淡的亮黄色

保持-78℃搅拌30min用细长针头吸取少量监测反映

将吸出的的反应液滴进盛有饱和氯化铵溶液的子弹管中，充分摇动淬灭

加少量EA（乙酸乙酯）剧烈摇动萃取，萃取液当做试样进行TLC监测反映

产物紫外较弱，用CAM或PMA显色

反应完毕后加入饱和氯化铵溶液淬灭，恢复室温充分搅拌

分去有机相保留，水相用DCM或EA萃取三次，合并有机相，有机相用饱和碳酸氢钠溶液后用饱和氯化钠溶液洗涤

分出有机相无水硫酸钠干燥

抽滤后溶剂洗涤干燥剂，将溶液旋蒸去除溶剂浓缩

柱层析纯化分离

[修改于 5 年前 - 2020/05/15 14:33:39]

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Siberia_09_CIF3 十步芳草

十步芳草

4年8个月前 IP:辽宁

880757

1楼

赞一个

浪迹天涯

4年8个月前 IP:江苏

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顶啊

千古风流

4年8个月前 IP:上海

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感觉碳酸钾也许也够用。。。

好羡慕这么专业的-78度和氩气

做个荆芥内酯拿来卖吧

在下松田诚一

百炼成钢

作者

4年8个月前 IP:黑龙江

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引用m24h发表于3楼的内容

感觉碳酸钾也许也够用。。。好羡慕这么专业的-78度和氩气做个荆芥内酯拿来卖吧

碳酸钾不行那个酰胺氢攫不掉啊

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IP归属地：黑龙江

文章分类

有机合成实验

火箭发动机&喷气推动

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