Reaktion #1964176

Reaktionsgleichung

sodium hydrogen carbonate

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

thionyl chloride

→

title compound

Ausbeute 86.0%

3-[chloro(cyclohexyl)methyl]-2-ethyl-5-[4-(trifluoromethyl)phenyl]thiophene

Ausbeute 86.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled to 0° C.
2. 2
   Sonstigeto quench
3. 3
   Sonstigethe reaction
4. 4
   Extraktionthe mixture was extracted with ethyl acetate
5. 5
   WaschenThe extract was washed with brine
6. 6
   Trocknendried over magnesium sulfate
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   SonstigeThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio)

Vorschrift

To a solution of cyclohexyl{2-ethyl-5-[4-(trifluoromethyl)phenyl]thiophen-3-yl}methanol (2.29 g) synthesized in Example 69 (7) in toluene (25 mL) was added thionyl chloride (907 μL), and the mixture was stirred at 100° C. for 1 hr. The reaction mixture was cooled to 0° C., saturated aqueous sodium hydrogen carbonate solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio) to give the title compound (2.08 g, 86%) as a pale-brown solid.

Quelle