Nitromethane → HCID 22563942, compound

HRID 2297736Notes

Reaction equation

HRID 2297736 reaction equation
C1CCN2C(=NCCC2)CC1.[CH:12](/[C:15]1[CH:26]=[CH:25][CH:24]=[CH:23][C:16]=1[CH:17]=[CH:18][C:19]([O:21][CH3:22])=[O:20])=[CH:13]\[CH3:14].C(=O)(O)[O-].[Na+].[N+:32]([CH3:35])([O-:34])=[O:33]>>[CH:12](/[C:15]1[CH:26]=[CH:25][CH:24]=[CH:23][C:16]=1[CH:17]([CH2:35][N+:32]([O-:34])=[O:33])[CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:13]\[CH3:14]

Participants

5

Reactant 4

HCID 6375NitromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516892Sodium BicarbonateHCID 70161444HCID 70161444, compound

Product 1

HCID 22563942HCID 22563942, compoundYield 40%

Procedure

1,8-Diazabicyclo[5.4.0]-7-undecene (0.1 mL) was added to a solution (10 mL) of methyl 2-((E)-1-propenyl)cinnamate (102 mg, 0.50 mmol) in nitromethane, followed by-stirring at room temperature for 3 hours. Next, the reaction solution was added to a saturated aqueous solution of sodium bicarbonate under ice-cooling to neutralize the reaction solution, and the mixture was then extracted with diethyl ether. After the extract was washed with a saturated brine and then dried over sodium sulfate, the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developed with diethyl ether/hexane=1/4) to give methyl 3-[2-((E)-1-propenyl)phenyl]-4-nitrobutyrate (52 g, yield 40%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was then extracted with diethyl ether
  3. washAfter the extract was washed with a saturated brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (developed with diethyl ether/hexane=1/4)

Sources & evidence

ORD record
ord-267520cb67d2402c9cb2e7b47171dc30
Source dataset
uspto-grants-2002_12
Patent number
US06492392B1

Reaction notes

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