2-Nitropropane → HCID 86639392, compound

HRID 1685824Notes

Reaction equation

HRID 1685824 reaction equation
[N+](C(C)C)([O-])=[O:2].C[O-].[Na+].[Br:10][C:11]1[C:12]([CH2:25]Br)=[CH:13][C:14]([O:23][CH3:24])=[C:15]([CH:17]([CH3:22])[C:18]([O:20][CH3:21])=[O:19])[CH:16]=1>CO>[Br:10][C:11]1[C:12]([CH:25]=[O:2])=[CH:13][C:14]([O:23][CH3:24])=[C:15]([CH:17]([CH3:22])[C:18]([O:20][CH3:21])=[O:19])[CH:16]=1

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 10942334Sodium MethoxideHCID 67265374HCID 67265374, compound

Product 1

HCID 86639392HCID 86639392, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 2-nitropropane (210 mg) in methanol (5 ml) was added sodium methoxide (130 mg), and the solution was refluxed by heating for 0.5 hour, and then cooled on ice. To this reaction mixture was added a solution of methyl 2-(5-bromo-4-bromomethyl-2-methoxyphenyl)propionate (860 mg) obtained above in methanol (4 ml), and the mixture was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with 1.0 M aqueous hydrochloric acid, water, and saturated brine, and then dried over sodium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by column chromatography (hexane/ethyl acetate=7/1) to give the title compound (540 mg).

Workup

  1. temperaturethe solution was refluxed
  2. temperatureby heating for 0.5 hour
  3. temperaturecooled on ice
  4. customThe solvent was evaporated under reduced pressure, and water
  5. additionwas added to the residue
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed successively with 1.0 M aqueous hydrochloric acid, water, and saturated brine
  8. dry with materialdried over sodium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe residue was purified by column chromatography (hexane/ethyl acetate=7/1)

Sources & evidence

ORD record
ord-7df543c7231f4f1fa19db977732ea75b
Source dataset
uspto-grants-2012_04
Patent number
US08148421B2

Reaction notes

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