Reaktion #66716

Reaktionsgleichung

Methyl magnesium chloride

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

→

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

Ausbeute 108.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched by addition of 1 N NH4Cl
2. 2
   Extraktionextracted with EtOAc
3. 3
   WaschenThe combined organic layers were washed with 1 N ammonium chloride, brine
4. 4
   Trocknendried over MgSO4
5. 5
   Einengenconcentrated under reduced pressure

Vorschrift

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%).

Quelle