Dimethylformamide → HCID 178500165, compound

HRID 1036524Notes

Reaction equation

HRID 1036524 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

HCID 178500165HCID 178500165, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-4d6eb0fc0ead4113b04e4ab65c0763f6
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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