반응 #1060703

반응 방정식

ether

(S)-4-[4-(2-propoxypropanoyloxy)phenyl]benzoyl chloride

(1R,2S)-1-cyano-2-hexyl-1-(4-hydroxyphenyl)cyclopropane

pyridine

→

desired compound

수율 46.0%

4-((1R,2S)-1-cyano-2-hexylcyclopropyl)phenyl (S)-4-[4-(2-propoxypropanoyloxy)phenyl]benzoate

수율 46.0%

용매

dichloromethane

반응 조건

후처리

1. 1
   온도under reflux
2. 2
   온도The reaction mixture was cooled
3. 3
   기타The ethanol phase was separated
4. 4
   세척washed with diluted hydrochloric acid, water
5. 5
   건조saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate
6. 6
   기타The solvent was removed by evaporation
7. 7
   기타the residue was purified by silica gel column chromatography (solvent: hexane/ethyl acetate=5/1)
8. 8
   기타Recrystallization from ethanol
9. 9
   기타afforded

실험 절차

In 10 ml of dichloromethane were dissolved 83 mg of (S)-4-[4-(2-propoxypropanoyloxy)phenyl]benzoyl chloride and 65 mg of (1R,2S)-1-cyano-2-hexyl-1-(4-hydroxyphenyl)cyclopropane. To this solution was added 0.5 ml of pyridine. The resulting mixture was stirred for 3 hours under reflux. The reaction mixture was cooled, and then ether was added thereto. The ethanol phase was separated, washed with diluted hydrochloric acid, water, and then saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. The solvent was removed by evaporation and the residue was purified by silica gel column chromatography (solvent: hexane/ethyl acetate=5/1). Recrystallization from ethanol afforded, thereby obtaining 61 mg of the desired compound as colorless crystals.

출처