Nitromethane → HCID 22563942、化合物

反応式

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]

参加物

反応物 4

HCID 6375Nitromethane

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

HCID 516892Sodium Bicarbonate

HCID 70161444HCID 70161444、化合物

生成物 1

HCID 22563942HCID 22563942、化合物収率 40%

実験手順

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%).