Reaction #1060703

Reaction equation

ether

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

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

pyridine

→

desired compound

Yield 46.0%

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

Yield 46.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   Temperatureunder reflux
2. 2
   TemperatureThe reaction mixture was cooled
3. 3
   OtherThe ethanol phase was separated
4. 4
   Washwashed with diluted hydrochloric acid, water
5. 5
   Dryingsaturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate
6. 6
   OtherThe solvent was removed by evaporation
7. 7
   Otherthe residue was purified by silica gel column chromatography (solvent: hexane/ethyl acetate=5/1)
8. 8
   OtherRecrystallization from ethanol
9. 9
   Otherafforded

Procedure

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.

Source