HRID720769

反应详情

EQUATION

反应方程式

HRID 720769 的结构方程式

AUXILIARIES

试剂、催化剂与溶剂

3

PROCEDURE

实验过程

Under argon atmosphere, a solution of cerium chloride (4.55 g, 3.0 equivalents) in THF (25 mL) was stirred at room temperature (25° C.) for 30 minutes. After sodium borohydride (0.72 g, 3.1 equivalents) was added, the mixture was stirred at room temperature for 1 hour. Then, bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphine oxide (3.0 g, 6.16 mmol) synthesized in Reference Example 3 and lithium aluminum hydride (0.28 g, 1.2 equivalents) were successively added at 5° C., and the mixture was stirred at room temperature for 18 hours. After water (10 mL) was added at 3° C. and toluene (30 mL) and 6M-HCl (20 mL) were then added, the mixture was stirred at room temperature for 30 minutes. The reaction solution was allowed to separate into layers. An aqueous layer was extracted with toluene (30 mL). Organic layers were combined, washed with a 5% NaCl aqueous solution (20 mL), dried over anhydrous magnesium sulfate and then naturally filtered. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (alumina 25 g, n-hexane). The residue was recrystallized from heptane to obtain the title compound (1.18 g, white crystal). Yield 39.6%, mp. 134.7° C.

WORKUP

后处理

  1. additionwere successively added at 5° C.
  2. stirringthe mixture was stirred at room temperature for 18 hours
  3. stirringthe mixture was stirred at room temperature for 30 minutes
  4. customto separate into layers
  5. extractionAn aqueous layer was extracted with toluene (30 mL)
  6. washwashed with a 5% NaCl aqueous solution (20 mL)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationnaturally filtered
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customThe residue was purified by column chromatography (alumina 25 g, n-hexane)
  11. customThe residue was recrystallized from heptane