HCID 58762226, compound → 1-(4-Methoxyphenyl)pentan-3-one
Reaction equation
[CH2:1]([Mg]Br)[CH3:2].CON(C)[C:8](=[O:19])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1>C1COCC1>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH2:9][C:8](=[O:19])[CH2:1][CH3:2])=[CH:12][CH:13]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Ethylmagnesium bromide (10.8 mL, 10.8 mmol, 1M soln in THF) was added to a cooled −78° C. solution of N-Methoxy-3-(4-methoxy-phenyl)-N-methyl-propionamide (2 g, 8.96 mmol, from Step 1) dissolved in THF (20 mL). The reaction mixture was stirred for 60 min. The reaction was quenched with saturated NH4Cl and extracted with EtOAc. The organic layer was washed brine, dried over Na2SO4 and concentrated to a clear oil. The residue was purified by silica gel chromatography (5% EtOAc in hexanes) to give the title compound as a clear oil (0.87 g, 50%).