반응 #1964423

반응 방정식

2-methyl-5-[4-(trifluoromethyl)phenyl]thiophene-3-carbaldehyde

cyclohexylmagnesium bromide tetrahydrofuran

Hydrochloric acid

→

title compound

수율 65.0%

cyclohexyl{2-methyl-5-[4-(trifluoromethyl)phenyl]thiophen-3-yl}methanol

수율 65.0%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   기타to quench
2. 2
   기타the reaction
3. 3
   추출the mixture was extracted with ethyl acetate
4. 4
   세척The extract was washed with saturated brine
5. 5
   건조dried over magnesium sulfate
6. 6
   농축concentrated under reduced pressure
7. 7
   기타The residue was purified by silica gel column chromatography (25% ethyl acetate/hexane)
8. 8
   기타purified by NH-silica gel column chromatography (ethyl acetate)

실험 절차

To a solution of 2-methyl-5-[4-(trifluoromethyl)phenyl]thiophene-3-carbaldehyde (2.33 g) synthesized above in tetrahydrofuran (50 mL) was added dropwise 1.0M cyclohexylmagnesium bromide-tetrahydrofuran solution (12.9 mL) at 0° C., and the mixture was stirred for 1 hr. 1N Hydrochloric acid was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (25% ethyl acetate/hexane), and then purified by NH-silica gel column chromatography (ethyl acetate) to give the title compound (1.98 g, 65%) as a white solid.

출처