Ethanol → 2,2-dimethyl-5-(4-nitrophenyl)furan-3(2H)-one

反応式

O[C:2]([CH3:17])([CH3:16])[C:3]#[C:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)=[O:6].C(NCC)C.C([OH:25])C>>[CH3:16][C:2]1([CH3:17])[C:3](=[O:25])[CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=2)[O:6]1

参加物

反応物 3

HCID 702Ethanol2 回

HCID 8021Diethylamine

HCID 593548124-Hydroxy-4-methyl-1-(4-nitrophenyl)pent-2-yn-1-one

生成物 1

HCID 593547702,2-dimethyl-5-(4-nitrophenyl)furan-3(2H)-one収率 92%

実験手順

To a stirred solution of 4-hydroxy-4-methyl-1-(4-nitrophenyl)pent-2-yn-1-one (1.74 g, 7.46 mmol, 1 eq) in ethanol (30 mL), a solution of diethylamine (778 mg, 7.46 mmol, 1 eq) in EtOH (5 mL) was added dropwise at RT. The reaction mixture was then stirred for additional 90 min. The ethanol was removed, and the mixture was then diluted with EtOAc (100 mL). The combined organic layers were washed with water (50 mL) and brine (20 mL), dried over Na2SO4, filtered, and concentrated in vacuo to afford 2,2-dimethyl-5-(4-nitrophenyl)furan-3(2H)-one (1.6 g, 92%) which was used in the next step without further purification.