반응 #1964176

반응 방정식

sodium hydrogen carbonate

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

thionyl chloride

→

title compound

수율 86.0%

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

수율 86.0%

용매

toluene

반응 조건

후처리

1. 1
   온도The reaction mixture was cooled to 0° C.
2. 2
   기타to quench
3. 3
   기타the reaction
4. 4
   추출the mixture was extracted with ethyl acetate
5. 5
   세척The extract was washed with brine
6. 6
   건조dried over magnesium sulfate
7. 7
   농축concentrated under reduced pressure
8. 8
   기타The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio)

실험 절차

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.

출처