반응 #311431

반응 방정식

2,3,6-trichloro-4-methoxybenzyl 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-(2,3,6-trichloro-4-methoxyphenyl)-4-fluoro-3,7-dimethyl-2,4,6,8-nonatetraenoate

수율 58.0%

용매

toluene

반응 조건

후처리

1. 1
   workup.ADDITIONA mixture of 2.36 g
2. 2
   여과the resulting crude product was filtered through 150 g
3. 3
   세척Elution with methylene chloride
4. 4
   기타gave 2.48 g
5. 5
   기타Recrystallization of this material from methylene chloride-isopropyl ether
6. 6
   기타yielded 2.21 g

실험 절차

A mixture of 2.36 g. (9.54 mmol) of 2,3,6-trichloro-4-methoxybenzyl triphenylphosphonium chloride and 2.0 g. (8.93 mmol) of ethyl (E,Z,E)-4-fluoro-3,7-dimethyl-8-oxo-2,4,6-octatrienoate in 200 ml. of toluene and 150 ml. of 1,2-butylene oxide was heated at 85°-90° C. under argon for 18 hours. The mixture was worked up in the usual manner and the resulting crude product was filtered through 150 g. of silica gel. Elution with methylene chloride gave 2.48 g. of a yellow crystalline substance. Recrystallization of this material from methylene chloride-isopropyl ether yielded 2.21 g. (58% yield) of ethyl (E,Z,E,E)-9-(2,3,6-trichloro-4-methoxyphenyl)-4-fluoro-3,7-dimethyl-2,4,6,8-nonatetraenoate as yellow crystals, mp. 140°-142.5° C.

출처