反応 #6697

反応方程式

3-chloroaniline

1,3,3-trimethoxybutane

→

desired product

7-chlorolepidine

溶媒

ethanol

反応条件

後処理

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

実験手順

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.

出典