反应 #1702168

反应方程式

lithium aluminum hydride

ethyl 4-oxocyclohexanecarboxylate

diethyl ether

diethyl ether

→

4-Methylenecyclohexanecarboxylic acid ethyl ester

反应条件

后处理

1. 1
   温度The reaction is heated
2. 2
   温度to reflux for 2 h after which it
3. 3
   温度is cooled in an ice bath
4. 4
   其他quenched with by subsequent additions of isopropanol, 50% NaOH in water, and water
5. 5
   过滤The mixture is then filtered
6. 6
   洗涤the filter cake is washed with excess diethyl ether
7. 7
   洗涤The filtrate is then washed with water and brine
8. 8
   干燥dried over sodium sulfate
9. 9
   浓缩concentrated in vacuo
10. 10
    其他to provide a clear oil that
11. 11
    其他is used without further purification

实验过程

4-Methylenecyclohexanecarboxylic acid ethyl ester is prepared from the Wittig reaction on ethyl 4-oxocyclohexanecarboxylate using Method 3. This ester is reduced to compound III-5 according to the following procedure: To a solution of lithium aluminum hydride (4.0 equiv) in diethyl ether (1.0 M with respect to hydride) is added ethyl 4-oxocyclohexanecarboxylate in diethyl ether (2.0 M with respect to ester). The reaction is heated to reflux for 2 h after which it is cooled in an ice bath and quenched with by subsequent additions of isopropanol, 50% NaOH in water, and water. The mixture is then filtered and the filter cake is washed with excess diethyl ether. The filtrate is then washed with water and brine, dried over sodium sulfate, and concentrated in vacuo to provide a clear oil that is used without further purification.

来源