Dimethylformamide → HCID 178500165、化合物

HRID 2389183ノート

反応式

HRID 2389183 の反応式
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]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 7294Methyl AcrylateHCID 11430Potassium CarbonateHCID 178435549HCID 178435549、化合物

生成物 1

HCID 178500165HCID 178500165、化合物

試薬・触媒・溶媒 2

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e5f79036b14947b19a3f6af78028afc4
出典データセット
uspto-grants-2012_09
特許番号
US08269043B2

反応ノート

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