Boron tribromide → HCID 69151947, compound

Participants

Reaction Steps

260 mg (0.75 mmol) of methyl trans-2-(2,6-dimethoxy-4-pentylphenyl)cyclo-hexanecarboxylate were initially introduced in 10 ml of dichloromethane, and 191 μl (2 mmol) of boron tribromide were added at −70° C. After 20 min, the cooling was removed, and the batch was hydrolysed at 0° C. using sat. sodium hydrogencarbonate soln. The mixture was extracted with dichloromethane, dried over sodium sulfate and evaporated. Chromatography with heptane/ethyl acetate (7:1) gave 100 mg (45%) of (6aR*,10aR*)-1-hydroxy-3-pentyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-6-one as a colourless solid.

Provenance & Evidence