Reaction #1060702

Reaction equation

hydrochloric acid

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

potassium t-butoxide

4-(4-octyloxyphenyl)benzyl bromide

→

desired compound

Yield 95.1%

(1R,2S)-1-cyano-2-hexyl-1-[4-{4-(4-octyloxyphenyl)phenylmethoxy}phenyl]cyclopropane

Yield 95.1%

Solvents

DMF

DMF

Conditions

Workup

1. 1
   Otheras obtained in Example 11
2. 2
   workup.STIRRINGthis mixture was stirred for 6 hours
3. 3
   Extractionthe resulting mixture was subjected to extraction with 50 ml of ether
4. 4
   WashThe resulting organic layer was washed with water
5. 5
   Dryingwith saturated 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=10/1)

Procedure

In 10 ml of DMF was dissolved 49 mg of (1R,2S)-1-cyano-2-hexyl-1-(4-hydroxyphenyl)cyclopropane as obtained in Example 11. Thereto was added 34 mg of potassium t-butoxide, and the resulting mixture was stirred at room temperature for 70 minutes. Thereto was added dropwise a solution of 98 mg of 4-(4-octyloxyphenyl)benzyl bromide in 3 ml of DMF, and this mixture was stirred for 6 hours. Thereafter, 20 ml of 5% hydrochloric acid was added to the reaction mixture, and the resulting mixture was subjected to extraction with 50 ml of ether. The resulting organic layer was washed with water and then with 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=10/1), thereby obtaining 103 mg of the desired compound in the form of white crystals.

Source