Sodium Hydroxide → HCID 178437434, compound

Participants

Reaction Steps

Lithium aluminum hydride (23.3 mg, 0.616 mmol) was suspended in THF (0.6 mL), and a solution of aluminum chloride (41.1 mg, 0.308 mmol) in THF (0.6 mL) was added to the suspension at 0° C., followed by stirring for 5 minutes. Then the mixture was added with a solution of Compound 148 (60.0 mg, 0.154 mmol) in THF (1.4 mL) followed by stirring at 0° C. for 0.5 hours. The reaction mixture was added with 2 mol/L aqueous sodium hydroxide solution and extracted with ethyl acetate twice. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methanol:chloroform=1:49). The obtained compound was crystallized from diethyl ether to obtain Compound 152 (cis:trans=15:85, 38.1 mg, 0.0971 mmol, 63.2%).

Provenance & Evidence