Dimethylformamide → HCID 178500165, 화합물

HRID 1036524노트

반응식

HRID 1036524 반응식
C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[N+:12]([CH:15]([C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:27][C@H:28]3[CH2:33][CH2:32][C@H:31]([C:34]([F:37])([F:36])[F:35])[CH2:30][CH2:29]3)[CH:23]=2)[CH:18]=1)[CH3:16])([O-:14])=[O:13].[C:38]([O:42][CH3:43])(=[O:41])[CH:39]=[CH2:40]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH3:43][O:42][C:38](=[O:41])[CH2:39][CH2:40][C:15]([N+:12]([O-:14])=[O:13])([C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:27][C@H:28]3[CH2:29][CH2:30][C@H:31]([C:34]([F:37])([F:36])[F:35])[CH2:32][CH2:33]3)[CH:23]=2)[CH:18]=1)[CH3:16]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 7294Methyl AcrylateHCID 11430Potassium CarbonateHCID 178435549HCID 178435549, 화합물

생성물 1

HCID 178500165HCID 178500165, 화합물

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of potassium carbonate (78 mg, 0.56 mmol, Fisher), tetrabutylammonium hydrogen sulfate (10. mg, 0.029 mmol, Aldrich) and N,N-dimethylformamide (2.00 mL, Acros) was added 2-(1-nitro-ethyl)-6-(trans-4-trifluoromethyl-cyclohexyloxy)-naphthalene (0.159 g, 0.433 mmol). The mixture was stirred and methyl acrylate (50 μL, 0.56 mmol, Aldrich) was added. The mixture was stirred at room temperature. After 2 h, ethyl acetate was added and the solution was washed with saturated ammonium chloride, then saturated sodium chloride. The organics were dried over Na2SO4, filtered, concentrated. The residue was taken up in DCM, and silica gel was added. The solvent was removed and the residue was purified by silica gel chromatography (0-25% EtOAc in hexanes). Isolated was 98 mg (50%) of product (Rf=0.19 in 7:1 hexanes/ethyl acetate).

후처리

  1. stirringThe mixture was stirred at room temperature
  2. washthe solution was washed with saturated ammonium chloride
  3. dry with materialThe organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additionsilica gel was added
  7. customThe solvent was removed
  8. customthe residue was purified by silica gel chromatography (0-25% EtOAc in hexanes)
  9. customIsolated

출처 및 근거

ORD 기록
ord-4d6eb0fc0ead4113b04e4ab65c0763f6
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546359B2

반응 노트

불러오는 중…