반응 #980

반응 방정식

amide

N-Methyl-N-Methoxy-4-(3-indolyl)butyramide

benzylmagnesium chloride

→

ketone

수율 68.6%

Benzyl-3-(3-indolyl)propyl ketone

수율 68.6%

용매

THF

반응 조건

후처리

1. 1
   기타The reaction was quenched with 5% KHSO4
2. 2
   추출extracted into ether
3. 3
   세척The combined ethereal layers were washed with brine
4. 4
   건조dried over MgSO4
5. 5
   세척Flash chromatography (elution with 25% ether in hexane)

실험 절차

To a solution of 147 mg (0.60 mmol) of amide 139 in 4.0 mL of THF at -78° C. was added 1.31 mL (1.31 mmol) of benzylmagnesium chloride (1.0M in Et2O) and the reaction mixture was allowed to warm to room temperature and stir for 3 h. The reaction was quenched with 5% KHSO4 and extracted into ether. The combined ethereal layers were washed with brine and dried over MgSO4. Flash chromatography (elution with 25% ether in hexane) gave 108 mg of the ketone 140. 1H NMR consistent with structure.

출처