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

HRID 2243071Notes

Reaction equation

HRID 2243071 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 h, 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. The combined EtOAc layers were which washed with brine, dried over anhydrous MgSO4, and concentrated to give an oil that was chromatographed on silica gel (100% DCM followed by gradient elution to 50% EtOAc in DCM). The title compound (8.5 g) was obtained as a mobile oil. MS (ES) (M+H)+: 169 for C8H12CN2O2; NMR: 2.69 (s, 3H), 3.34 (s, 3H), 3.71 (m, 2H), 4.61 (m, 2H), 7.12 (s, 1H), 7.26 (s, 1H).

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
  5. washwashed with brine
  6. dry with materialdried over anhydrous 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-4ecdeebc4a054d5c81976a3e356c1542
Source dataset
uspto-grants-2010_03
Patent number
US07674801B2

Reaction notes

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