Reaktion #1964423

Reaktionsgleichung

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

cyclohexylmagnesium bromide tetrahydrofuran

Hydrochloric acid

→

title compound

Ausbeute 65.0%

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

Ausbeute 65.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto quench
2. 2
   Sonstigethe reaction
3. 3
   Extraktionthe mixture was extracted with ethyl acetate
4. 4
   WaschenThe extract was washed with saturated brine
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigeThe residue was purified by silica gel column chromatography (25% ethyl acetate/hexane)
8. 8
   Sonstigepurified by NH-silica gel column chromatography (ethyl acetate)

Vorschrift

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.

Quelle