HRID1595926

反应详情

EQUATION

反应方程式

HRID 1595926 的结构方程式

AUXILIARIES

试剂、催化剂与溶剂

2

CONDITIONS

反应条件

温度
0 °C

PROCEDURE

实验过程

6-Benzyloxy-2-[4-[bis(trimethylsilyl)amino]phenyl]benzo[b]thiophen-3-yl 3-methoxy-4-[(1-pyrrolidinyl)methyl]phenyl ketone (0.73 g) was dissolved in THF (10 mL), cooled to 0° C. in an ice bath before treated with lithium aluminum hydride (110 mg) at 0° C. for 1 h, then quenched with water(1 mL) and sodium hydroxide (1.0 M, 1 mL). Stirring continued for 30 min. The reaction mixture was diluted with brine(30 mL) and extracted with dichloromethane (20 mL×3). The combined organic layers were dried with sodium sulfate and concentrated in vacuo to give the crude alcohol. This material was dissolved in dichloromethane (15 mL), treated with triethylsilane (1.5 mL) and trifluroacetic acid (1.5 mL) sequentially, allowed to stir at ambient temperature for 1.5 h, and concentrated under reduced pressure. The residue was extracted with dichloromethane (20 mL×3) from saturated aqueous sodium bicarbonate (30 mL). The combined organic layers were dried with sodium sulfate and concentrated. Chromatography with Et3N:MeOH:EtOAc (5:5:90) afforded the title compound as a yellow foam (0.53 g).

WORKUP

后处理

  1. customquenched with water(1 mL) and sodium hydroxide (1.0 M, 1 mL)
  2. additionThe reaction mixture was diluted with brine(30 mL)
  3. extractionextracted with dichloromethane (20 mL×3)
  4. dry with materialThe combined organic layers were dried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give the crude alcohol
  7. stirringto stir at ambient temperature for 1.5 h
  8. concentrationconcentrated under reduced pressure
  9. extractionThe residue was extracted with dichloromethane (20 mL×3) from saturated aqueous sodium bicarbonate (30 mL)
  10. dry with materialThe combined organic layers were dried with sodium sulfate
  11. concentrationconcentrated