N-[4-(2-hydroxypropan-2-yl)-3-methoxyphenyl]acetamide synthesis

Yield:865306-00-9 100%

Reaction Conditions:

Stage #1: N-(4-acetyl-3-methoxyphenyl)acetamide;methylmagnesium chloride in tetrahydrofuran at 0 - 20; for 2.91667 h;
Stage #2: with ammonium chloride in tetrahydrofuran;

Steps:

64.2

Methyl magnesium chloride (49.9 ml, 150 mmol, 3 M solution in THF) in 100 ml THF was cooled to zero degrees C, and N-(4-Acetyl-3-methoxy-phenyl)-acetamide (14.1 g, 68 mmol) in 200 ml THF was added via cannula to over 25 minutes. The reaction mixture was stirred and allowed to warm to room temperature over 2.5 hours. The reaction was quenched by addition of 1 N NH₄Cl and extracted with EtOAc. The combined organic layers were washed with 1 N ammonium chloride, brine, dried over MgSO₄, and concentrated under reduced pressure to afford N-[4-(1-Hydroxy-1-methyl-ethyl)-3-methoxy-phenyl]-acetamide (16.4 g, 100%).

References:

US2005/209260,2005,A1 Location in patent:Page/Page column 146