反応 #623881

反応方程式

2

4-(Dimethoxy)methyl-5-hydroxymethyl(1,2-methylenedioxy)benzene

DMAD

AcOH

→

3

収率 176.5%

Dimethyl 1,4-Dihydro-1,4-epoxy-6,7-methylenedioxy-2,3-naphthalene-dicarboxylate

収率 176.5%

反応条件

後処理

1. 1
   その他Excess DMAD was removed by vacuum distillation, and flash chromatography (30% EtOAc/hexanes)

実験手順

The substrate 2 (23.7 g, 105 mmol) was dissolved in excess DMAD (251 g, 1.76 mol) and glacial AcOH (23.2 mL, 0.4 mol), and the mixture was stirred for 2 h at 80° C. Excess DMAD was removed by vacuum distillation, and flash chromatography (30% EtOAc/hexanes) gave 3 (56.4 g, 90%) as a yellow solid. On a smaller scale, 2 (5.53 g, 24.1 mmol) gave 3 in 92% yield (13.6 g): mp 117-119° C.; 1H NMR (300 MHz, CDCl3) δ 3.79 (s, 6H), 5.86 (s, 2H), 5.90 (d, J=1 Hz, 1H), 5.95 (d, J=1 Hz, 1H), 6.95 (s, 2H); 13C NMR (125 MHz, CDCl3) δ 53.0, 85.7, 102.2, 105.2, 141.4, 146.2, 152.5, 163.5. Anal. Calculated for C15H12O7: C, 59.21; H, 3.98. Found: C, 59.27; H, 4.11.

出典