Hydrochloric Acid → HCID 178419203, compound

Participants

Reaction Steps

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.

Provenance & Evidence