Reaction #1178420

Reaction equation

N-(1-formyl-1,2-dimethyl-propyl)-3-methoxy-2-methyl-benzamide

3-methylphenyl-magnesium bromide

→

N-[1-(hydroxy-m-tolyl-methyl)-1,2-dimethyl-propyl]-3-methoxy-2-methyl-benzamide

Yield 101.3%

Solvents

—

dry ice acetone

THF

Conditions

Workup

1. 1
   OtherAn oven-dried vial equipped with a stir bar
2. 2
   Otherwas flushed with N2
3. 3
   OtherThe reaction was quenched by addition of saturated aqueous NaHCO3 (5 mL)
4. 4
   workup.ADDITIONpoured onto a 10 mL Chem Elut cartridge
5. 5
   WashAfter 5 min the cartridge was eluted with CH2Cl2 (25 mL)
6. 6
   OtherThe eluate was evaporated

Procedure

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.

Source