Reaktion #980

Reaktionsgleichung

amide

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

benzylmagnesium chloride

→

ketone

Ausbeute 68.6%

Benzyl-3-(3-indolyl)propyl ketone

Ausbeute 68.6%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched with 5% KHSO4
2. 2
   Extraktionextracted into ether
3. 3
   WaschenThe combined ethereal layers were washed with brine
4. 4
   Trocknendried over MgSO4
5. 5
   WaschenFlash chromatography (elution with 25% ether in hexane)

Vorschrift

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.

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