反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
PROCEDURE
实验过程
Under an argon atmosphere, a solution of cerium chloride (7.69 g, 3.0 equivalents) in tetrahydrofuran (25 mL) was stirred at room temperature (25° C.) for 30 min. After addition of sodium borohydride (1.22 g, 3.1 equivalents), the mixture was stirred at room temperature for 1 hr. After bis(4-dimethylaminophenyl)-phosphine oxide (3.0 g, 10.4 mmoL) synthesized in Reference Example 6 and lithium aluminum hydride (0.47 g, 1.2 equivalents) were successively added to the mixture at 5° C., the mixture was stirred at room temperature for 3 hr. Water (20 mL) was added to the mixture at 3° C., and then toluene (40 mL) and 6M hydrochloric acid (10 mL) were added thereto, and the mixture was stirred at room temperature for 30 min. The reaction mixture was neutralized with sodium hydroxide, and the mixture was partitioned. The aqueous layer was extracted with tetrahydrofuran (50 mL). The combined organic layer was successively washed with 5% brine (20 mL). The organic layer was dried over anhydrous magnesium sulfate and filtered naturally, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel 5 g, n-hexane/ethyl acetate=1/1). The residue was recrystallized from n-heptane to give the title compound (0.61 g, white crystals). yield 20.5%. melting point 142.6° C.
WORKUP
后处理
- additionwere successively added to the mixture at 5° C.
- stirringthe mixture was stirred at room temperature for 3 hr
- stirringthe mixture was stirred at room temperature for 30 min
- customthe mixture was partitioned
- extractionThe aqueous layer was extracted with tetrahydrofuran (50 mL)
- washThe combined organic layer was successively washed with 5% brine (20 mL)
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- filtrationfiltered naturally
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was purified by column chromatography (silica gel 5 g, n-hexane/ethyl acetate=1/1)
- customThe residue was recrystallized from n-heptane