N-(2,3-Dimethyl-1-oxobutan-2-yl)-3-methoxy-2-methylbenzamide → N-[1-(hydroxy-m-tolyl-methyl)-1,2-dimethyl-propyl]-3-methoxy-2-methyl-benzamide

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Reaction Steps

An oven-dried vial equipped with a stir bar was flushed with N2, charged with N-(1-formyl-1,2-dimethyl-propyl)-3-methoxy-2-methyl-benzamide (IX, R1=2-Me-3-MeO—Ph, R2=i-Pr, R3=Me, 131 mg, 0.5 mmol) in dry THF (1 mL) and cooled in dry ice acetone. 3-methylphenyl-magnesium bromide (1.0 M, 2 mL, 2.0 mmol) was added and the mixture was stirred at room temperature for 2 hours. The reaction was quenched by addition of saturated aqueous NaHCO3 (5 mL) and poured onto a 10 mL Chem Elut cartridge. After 5 min the cartridge was eluted with CH2Cl2 (25 mL). The eluate was evaporated to leave a secondary alcohol, N-[1-(hydroxy-m-tolyl-methyl)-1,2-dimethyl-propyl]-3-methoxy-2-methyl-benzamide (VIII, R1=2-Me-3-MeO—Ph, R2 =i-Pr, R3=Me, R4=3-Me—Ph, 180 mg). 1H and 13C NMR showed complete consumption of aldehyde.

Provenance & Evidence