Réaction #66716

Équation de réaction

Methyl magnesium chloride

N-(4-Acetyl-3-methoxy-phenyl)-acetamide

→

N-[4-(1-Hydroxy-1-methyl-ethyl)-3-methoxy-phenyl]-acetamide

Rendement 108.0%

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   AutreThe reaction was quenched by addition of 1 N NH4Cl
2. 2
   Extractionextracted with EtOAc
3. 3
   LavageThe combined organic layers were washed with 1 N ammonium chloride, brine
4. 4
   Séchagedried over MgSO4
5. 5
   Concentrationconcentrated under reduced pressure

Mode opératoire

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%).

Source