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

HRID 655751
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HRID 655751 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 537505N-Methoxy-N-methylacetamideHCID 143668401-(2-methoxyethyl)-1H-imidazoleHCID 178418339Butyllithium

생성물 1

HCID 59208500HCID 59208500, 화합물수율 82.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-b13b61f6cc1a4775b1e95b12e0c8e98f
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08071605B2

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