Reaction #1060701

Reaction equation

ether

4-(4-octyloxyphenyl)benzoyl chloride

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

pyridine

→

desired compound

Yield 36.8%

4-((1R,2S)-1-cyano-2-hexylcyclopropyl)phenyl 4-(4-octyloxyphenyl)benzoate

Yield 36.8%

Solvents

dichloromethane

Conditions

Workup

1. 1
   Otheras obtained in Example 11
2. 2
   Temperaturewith refluxing
3. 3
   Temperaturecooled
4. 4
   Washthe resulting mixture was washed with diluted hydrochloric acid, water, and saturated sodium chloride aqueous solution
5. 5
   Dryingdried over anhydrous sodium sulfate
6. 6
   OtherThe solvent was removed by evaporation
7. 7
   Otherthe residue was separated
8. 8
   Otherpurified by silica gel column chromatography (solvent: hexane/ethyl acetate=5/1)

Procedure

In 8 ml of dichloromethane were dissolved 66 mg of 4-(4-octyloxyphenyl)benzoyl chloride and 36 mg of (1R,2S)-1-cyano-2-hexyl-1-(4-hydroxyphenyl)cyclopropane as obtained in Example 11. Thereto was added 0.5 ml of pyridine. The resulting mixture was stirred for 8 hours with refluxing, and then cooled. Thereafter, 50 ml of ether was added to the reaction mixture, and the resulting mixture was washed with diluted hydrochloric acid, water, and saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. The solvent was removed by evaporation, and the residue was separated and purified by silica gel column chromatography (solvent: hexane/ethyl acetate=5/1). Thus, 30 mg of the desired compound was obtained as colorless crystals.

Source