反应 #6697

反应方程式

3-chloroaniline

1,3,3-trimethoxybutane

→

desired product

7-chlorolepidine

溶剂

ethanol

反应条件

后处理

1. 1
   其他preheated to 60° C.
2. 2
   温度The resulting mixture was refluxed for two hours
3. 3
   其他The volatile matrials were then removed in vacuo
4. 4
   其他The resulting mixture was partitioned between water and diethyl ether (3 times)
5. 5
   干燥The combined ether layer was dried over magnesium sulfate
6. 6
   其他Rotary evaporation of the ether solution
7. 7
   其他gave a dark liquid
8. 8
   workup.ADDITIONThe liquid was added to a silica gel column
9. 9
   洗涤eluted with hexane/ethyl acetate (3:1)

实验过程

To a mixture containing 3-chloroaniline (1.59 g), ferric chloride hexahydrate (5.4 g), zinc chloride (0.2 g), ethanol (20 ml of 95% aqueous solution) preheated to 60° C. was added 1,3,3-trimethoxybutane (1.48 g). The resulting mixture was refluxed for two hours and allowed to stand overnight. The volatile matrials were then removed in vacuo and the residue rendered basic with 10% aqueous sodium hydroxide. The resulting mixture was partitioned between water and diethyl ether (3 times). The combined ether layer was dried over magnesium sulfate. Rotary evaporation of the ether solution gave a dark liquid. The liquid was added to a silica gel column and eluted with hexane/ethyl acetate (3:1) to give the desired product as tan crystals.

来源