HRID896831

反应详情

EQUATION

反应方程式

HRID 896831 的结构方程式

CONDITIONS

反应条件

温度
0 °C

PROCEDURE

实验过程

A solution of furanone (13) (1.2 g, 5.88 mmols) and benzophenone (108 mg, 0.588 mmols) in [1,3]-dioxolane (108 mg) was degassed for 40 min in a stream of argon. The mixture then was irradiated using one 450 watt ACE glass medium pressure mercury lamp, from a distance of 15 cm, for 9 hours. Progress of this reaction was observed via 1H-NMR. As the reaction mixture was degassed, and throughout all of the irradiation time, the reaction flask was held in a water cooled cooling mantel. The temperature of the cooling water was constantly maintained near 0° C. Upon completion of the reaction, solvent was removed under reduced pressure, followed by column chromatography on silica gel (35% EtOAc in hexanes as the eluent), yielding the title compound (1.34 g, 82%) as a clear oil, Rf=0.14 (30% EtOAc in hexanes), [α]25D 16.5° (c 1.2, CHCl3); 1H-NMR (500 MHz, CDCl3) δ: 2.50 (dd, 1H, J=3.9, 12.9 Hz), 2.70-2.79 (m, 2H), 3.58 (dd, 1H, J=3.5, 7.2 Hz), 3.75 (dd, 1H, J=2.8, 7.9 Hz), 3.87-3.92 (m, 2H), 3.97-4.00 (m, 2H), 4.51 (d, 1H, J=11.9 Hz), 4.57-4.61 (m, 2H), 4.88 (d, 1H, J=3.6 Hz), 7.26-7.36 (m, 5H); 13C-NMR (125.8 MHz, CDCl3) δ: 30.39, 40.53, 65.77, 71.74, 73.99, 79.52, 104.14, 128.00, 128.89, 138.07, 176.79.

WORKUP

后处理

  1. customThe mixture then was irradiated
  2. customAs the reaction mixture was degassed
  3. temperaturecooled
  4. temperaturecooling mantel
  5. customUpon completion of the reaction, solvent
  6. customwas removed under reduced pressure