Reaction #980

Reaction equation

amide

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

benzylmagnesium chloride

→

ketone

Yield 68.6%

Benzyl-3-(3-indolyl)propyl ketone

Yield 68.6%

Solvents

THF

Conditions

Workup

1. 1
   OtherThe reaction was quenched with 5% KHSO4
2. 2
   Extractionextracted into ether
3. 3
   WashThe combined ethereal layers were washed with brine
4. 4
   Dryingdried over MgSO4
5. 5
   WashFlash chromatography (elution with 25% ether in hexane)

Procedure

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.

Source