반응 #1060702

반응 방정식

hydrochloric acid

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

potassium t-butoxide

4-(4-octyloxyphenyl)benzyl bromide

→

desired compound

수율 95.1%

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

수율 95.1%

용매

DMF

DMF

반응 조건

후처리

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

실험 절차

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.

출처