反应详情

温度

0 °C

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.

1. additionBorane-THF complex (0.95 mL, 9.89 mmol) was added via syringe
2. extractionafter 30 minutes the reaction mixture was extracted with ethyl acetate
3. washThe combined extracts were washed with water and brine
4. dry with materialdried over sodium sulfate
5. filtrationFiltration and concentration
6. customprovided the crude product which
7. customwas purified by chromatography on silica gel eluting with 10 to 30% EtOAc in hexanes