반응 #311430

반응 방정식

6-chloro-4-methoxy-2,3-dimethylbenzyl triphenylphosphonium chloride

ethyl (E,Z,E)-4-fluoro-3,7-dimethyl-8-oxo-2,4,6-octatrienoate

1,2-butylene oxide

→

ethyl (E,Z,E,E)-9-(6-chloro-4-methoxy-2,3-dimethylphenyl)-4-fluoro-3,7-dimethyl-2,4,6,8-nonatetraenoate

수율 35.0%

용매

ether

반응 조건

후처리

1. 1
   workup.ADDITIONA mixture of 6.0 g
2. 2
   기타to give 13.53 g
3. 3
   기타This material was chromatographed on 300 g
4. 4
   세척Elution with 1:4 ether-petroleum ether
5. 5
   기타yielded 4.65 g
6. 6
   기타Recrystallization of this material from methylene chloride-petroleum ether
7. 7
   기타afforded 1.67 g

실험 절차

A mixture of 6.0 g. (12.46 mmol) of 6-chloro-4-methoxy-2,3-dimethylbenzyl triphenylphosphonium chloride and 2.71 g. of ethyl (E,Z,E)-4-fluoro-3,7-dimethyl-8-oxo-2,4,6-octatrienoate in 15 ml. of 1,2-butylene oxide was heated at 110° C. in a sealed tube for 60 hours. The resulting mixture was worked up with ether in the usual manner to give 13.53 g. of crude product. This material was chromatographed on 300 g. of silica gel. Elution with 1:4 ether-petroleum ether yielded 4.65 g. of yellow crystals. Recrystallization of this material from methylene chloride-petroleum ether afforded 1.67 g. (35% yield) of pure ethyl (E,Z,E,E)-9-(6-chloro-4-methoxy-2,3-dimethylphenyl)-4-fluoro-3,7-dimethyl-2,4,6,8-nonatetraenoate as yellow crystals, mp. 126°-128° C.

출처