HCID 13221159, compound → HCID 59598542, compound

HRID 38438Notes

Reaction equation

HRID 38438 reaction equation
[CH3:1][Mg]Cl.[C:4]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:16])[CH3:15])=[CH:9][C:8]=1[O:17][CH3:18])(=[O:6])[CH3:5]>C1COCC1>[OH:6][C:4]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:16])[CH3:15])=[CH:9][C:8]=1[O:17][CH3:18])([CH3:1])[CH3:5]

Participants

4

Reactant 2

HCID 13221159HCID 13221159, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 59598542HCID 59598542, compoundYield 108%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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%).

Workup

  1. customThe reaction was quenched by addition of 1 N NH4Cl
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with 1 N ammonium chloride, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-941d72783dc44221a2d929e62c2ae8a5
Source dataset
uspto-grants-2013_09
Patent number
US08524725B2

Reaction notes

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