Benzyl Bromide → 5-(Dibenzylamino)-2-benzofuran-1(3H)-one

反応式

[NH2:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[CH:3]=1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH:20](N(C(C)C)CC)([CH3:22])[CH3:21].[CH2:29]1[CH2:33]O[CH2:31][CH2:30]1>>[CH2:12]([N:1]([CH2:31][C:30]1[CH:22]=[CH:20][CH:21]=[CH:33][CH:29]=1)[C:2]1[CH:3]=[C:4]2[C:5](=[CH:10][CH:11]=1)[C:6](=[O:9])[O:7][CH2:8]2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

反応物 4

HCID 7498Benzyl Bromide

HCID 8028Tetrahydrofuran

HCID 81531Diisopropylethylamine

HCID 7206695-Aminophthalide

生成物 1

HCID 220614885-(Dibenzylamino)-2-benzofuran-1(3H)-one収率 31%

反応条件

温度: 50 °C

実験手順

A mixture of 5-amino-2-benzofuran-1(3H)-one (100 mg, 0.67 mmol), benzyl bromide (319 μl, 2.68 mmol), and diisopropylethylamine (350 μl, 2.01 mmol) in THF (2.0 ml) was heated at 50° C. for 65 hours. The reaction was partitioned between water and EtOAc. The organic layer was washed with water, brine, dried with Na2SO4 and rotary evaporated. The yellow oil was triturated at room temperature with 10% EtOAc/hexane and then chromatographed (20% to 40% EtOAc/hexane gradient) to give 5-dibenzylamino-3H-isobenzofuran-1-one as a white solid (136 mg, 31%).