Hydrochloric Acid → HCID 178419208, compound

Participants

Reaction Steps

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.

Provenance & Evidence