Acetic Acid → HCID 178520752, compound

Participants

Reaction Steps

To a solution of benzyl 2-(4-oxocyclohexyl)acetate (2.64 g, 10.7 mmol) in methanol (50 mL) was added sodium borohydride (393 mg, 10.4 mmol) with stirring under ice cooling. After stirring at the same temperature for 2 h, the reaction mixture was adjusted to pH 4 with acetic acid (1 mL). The reaction mixture was concentrated under reduced pressure, and the residue thus obtained was diluted with ethyl acetate and water to separate the layers. The aqueous layer was extracted again with ethyl acetate, and the combined organic layer was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (hexane-ethyl acetate 3:1→2:1→1:1) to give 2.20 g of trans-4-benzyloxycarbonylmethyl-1-hydroxycyclohexane (yield: 82%) and 540 mg of cis-4-benzyloxycarbonylmethyl-1-hydroxycyclohexane (yield: 20%) as oil.

Provenance & Evidence