Benzyl cyclopent-3-enecarboxylate → Benzyl 3-hydroxycyclopentanecarboxylate

Participants

Reaction Conditions

Reaction Steps

The benzyl cyclopent-3-ene-1-carboxylate (2.0 g, 9.89 mmol) was dissolved in 20 mL of THF and cooled to 0° C. under nitrogen. Borane-THF complex (0.95 mL, 9.89 mmol) was added via syringe and the mixture was stirred for 30 minutes at 0° C. Sodium perborate tetrahydrate solution (100 mL of 0.33 M aqueous solution) was added, and after 30 minutes the reaction mixture was extracted with ethyl acetate. The combined extracts were washed with water and brine and then dried over sodium sulfate. Filtration and concentration provided the crude product which was purified by chromatography on silica gel eluting with 10 to 30% EtOAc in hexanes to provide benzyl 3-hydroxycyclopentanecarboxylate.

Provenance & Evidence