Sodium borohydride → HCID 12044322, compound

Participants

Reaction Conditions

Reaction Steps

Cerium trichloride heptahydrate (4.88 g, 13.1 mmol) and (trimethylsilyl)ethyl 4-(4-(2-methyl-6-oxocyclohexen-1-yl)but-3-en-1-ynyl)benzoate (Compound D, 500 mg, 1.31 mmol) were dissolved in ethanol (80 mL), cooled to 0° C. and treated with sodium borohydride (495 mg, 13.1 mmol) in three equal portions. The resulting solution was stirred in the dark for 20 minutes at 0° C. The excess hydride was quenched by the addition of saturated aqueous NH4Cl and the mixture was extracted 3 times with ethyl acetate. The combined organic layers were washed with water, and brine, dried (MgSO4), filtered and the solvents were removed in vacuo. The residue was purified by silica gel chromatography using a solution of hexane and ethyl acetate in a 5 to 1 ratio, respectively, to give the racemic title compound as a yellow oil.

Provenance & Evidence