Dimethylformamide → HCID 178500163, compound

HRID 1036469Notes

Reaction equation

HRID 1036469 reaction equation
C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[C:12]([CH:16]1[CH2:21][CH2:20][CH:19]([O:22][C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[C:28]([CH:33]([N+:35]([O-:37])=[O:36])[CH3:34])[CH:29]=3)[CH:24]=2)[CH2:18][CH2:17]1)([CH3:15])([CH3:14])[CH3:13].[C:38]([O:42][CH3:43])(=[O:41])[CH:39]=[CH2:40].[Cl-].[NH4+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(OC(=O)C)C.O>[C:12]([C@H:16]1[CH2:21][CH2:20][C@H:19]([O:22][C:23]2[CH:24]=[C:25]3[C:30](=[CH:31][CH:32]=2)[CH:29]=[C:28]([C:33]([N+:35]([O-:37])=[O:36])([CH3:34])[CH2:40][CH2:39][C:38]([O:42][CH3:43])=[O:41])[CH:27]=[CH:26]3)[CH2:18][CH2:17]1)([CH3:13])([CH3:14])[CH3:15]

Participants

9

Reactant 5

HCID 6228DimethylformamideHCID 7294Methyl AcrylateHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 866429012-(trans-4-Tert-butylcyclohexyloxy)-6-(1-nitroethyl)naphthalene

Product 1

HCID 178500163HCID 178500163, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

To a mixture of potassium carbonate (0.1783 g, 1.290 mmol), tetrabutylammonium hydrogen sulfate (0.005110 g, 0.01505 mmol) and N,N-dimethylformamide (3.00 mL, 38.7 mmol) was added 2-(4-tert-butyl-cyclohexyloxy)-6-(1-nitro-ethyl)-naphthalene (0.3821 g, 1.075 mmol). The mixture was stirred for 15 minutes, then methyl acrylate (0.1162 mL, 1.290 mmol) was added while maintaining the temperature at 20° C. (cool water bath). The mixture was stirred and allowed to reach room temperature. Stirring was continued (in slightly below room temperature water bath) for 2 hours and the reaction was monitored by HPLC. Ethylacetate and saturated aq. ammonium chloride were added and the layers were separated. The combined organic layer was dried over MgSO4, filtered, concentrated and purified by flash chromatography (0-20% EtOAc in hexanes) to give the title compound in 72% yield.

Workup

  1. stirringThe mixture was stirred
  2. customto reach room temperature
  3. stirringStirring
  4. customin slightly below room temperature
  5. customfor 2 hours
  6. customthe layers were separated
  7. dry with materialThe combined organic layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by flash chromatography (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-eb4d2c48f5fc4ac3b62a06d745089611
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

Loading…