N-Methoxy-N-methylacetamide → HCID 59208500, compound

HRID 655751Notes

Reaction equation

HRID 655751 reaction equation
C([Li])CCC.[CH3:6][O:7][CH2:8][CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1.CON(C)[C:18](=[O:20])[CH3:19]>C1COCC1>[CH3:6][O:7][CH2:8][CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[C:11]1[C:18](=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 537505N-Methoxy-N-methylacetamideHCID 14366840126301-59-5HCID 178418339Butyllithium

Product 1

HCID 59208500HCID 59208500, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 30 ml (75 mmol) of 2.5 M n-butyllithium in hexanes was added slowly to a solution of 8.48 g (61.3 mmol) 1-(2-Methoxyethyl)-1H-imidazole (WO 2003055876 A1 in 200 ml THF cooled in a dry ice-acetone bath. After stirring 1 hour, 8 ml (75 mmol) of N-methoxy-N-methylacetamide was added quickly, and the solution was allowed to warm to room temperature over 30 min. After quenching with aqueous NH4Cl, the mixture was diluted with water and extracted twice with EtOAc, which was washed with brine, dried (MgSO4) and concentrated to give an oil that was chromatographed on silica gel (100% DCM followed by gradient elution to 50% EtOAc in DCM). Product (8.5 g) was obtained as a mobile oil. MS (ES) (M+H)+: 169 for C8H12CN2O2

Workup

  1. temperaturecooled in a dry ice-acetone bath
  2. customAfter quenching with aqueous NH4Cl
  3. additionthe mixture was diluted with water
  4. extractionextracted twice with EtOAc, which
  5. washwas washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto give an oil that
  9. customwas chromatographed on silica gel (100% DCM followed by gradient elution to 50% EtOAc in DCM)

Sources & evidence

ORD record
ord-b13b61f6cc1a4775b1e95b12e0c8e98f
Source dataset
uspto-grants-2011_12
Patent number
US08071605B2

Reaction notes

Loading…