HRID413927

反应详情

EQUATION

反应方程式

HRID 413927 的结构方程式

AUXILIARIES

试剂、催化剂与溶剂

1

CONDITIONS

反应条件

温度
0 °C

PROCEDURE

实验过程

n-Hexyltriphenylphosphonium bromide (0.427 g, 1 mmol) was dried by azeotropic distillation from a benzene solution and then stirred in dry THF (10 mL) under nitrogen atmosphere. Sodium bis(trimethylsilyl)amide (1 M in THF, 1 mL, 1 mmol) was added and the ylide produced was stirred under nitrogen at 0° C. for 30 min. Intermediate 35 (0.276 g, 0.77 mmol) was added as a solution in THF (10 mL) under nitrogen. The mixture was stirred at rt overnight and partitioned between 1 N HCl (100 mL) and ethyl acetate (100 mL). The organic layer was dried over sodium sulfate, and evaporated to afford an oil which was chromatographed on SiO2 (230-400 mesh, 50 g), eluting with hexanes/ethyl acetate (4:1) to give the product (36) (0.15 g, 46%) as an oil: 1H NMR (CDCl3, 300 MHz) δ 7.63 (d, J=2.3 Hz, 1H), 7.56 (d, J=2.2 Hz, 1H), 7.20 (dt, J=2.3 Hz, 1H), 6.94 (d, J=8.6 Hz, 1H), 6.82 (d, J=8.7H, 1H), 5.96 (t, J=7.5 Hz, 1H), 3.90 (s, 3H), 3.84 (s, 3H), 3.83 (s, 6H), 2.05 (q, J=7.3 Hz, 2H), 1.39 (t, J=7.2 Hz, 2H), 1.22 (m, J=1.9 Hz, 2H), 0.83 (t, J=6.7 Hz, 3H); IR (neat) 2927, 2853, 1732, 1606, 1500, 1435, 1263 cm−1. Anal. (C25H30O6) C, H.

WORKUP

后处理

  1. customthe ylide produced
  2. stirringThe mixture was stirred at rt overnight
  3. custompartitioned between 1 N HCl (100 mL) and ethyl acetate (100 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated
  6. customto afford an oil which
  7. customwas chromatographed on SiO2 (230-400 mesh, 50 g)
  8. washeluting with hexanes/ethyl acetate (4:1)