반응 #6697

반응 방정식

3-chloroaniline

1,3,3-trimethoxybutane

→

desired product

7-chlorolepidine

용매

ethanol

반응 조건

후처리

1. 1
   기타preheated to 60° C.
2. 2
   온도The resulting mixture was refluxed for two hours
3. 3
   기타The volatile matrials were then removed in vacuo
4. 4
   기타The resulting mixture was partitioned between water and diethyl ether (3 times)
5. 5
   건조The combined ether layer was dried over magnesium sulfate
6. 6
   기타Rotary evaporation of the ether solution
7. 7
   기타gave a dark liquid
8. 8
   workup.ADDITIONThe liquid was added to a silica gel column
9. 9
   세척eluted with hexane/ethyl acetate (3:1)

실험 절차

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.

출처