Acetic Acid → HCID 67826073, compound

Participants

Reaction Steps

3-(3-Cyclopentyloxy-4-methoxyphenyl) -cyclopentan-1-ol, (predominantly cis, 160 mg, 0.58mmol) (E9) in freshly distilled tetrahydrofuran (5 ml) was stirred vigorously with diethylazodicarboxylate (96μl 0.58 mmol), triphenylphosphine (152 mg, 0.58mmol) and glacial acetic acid (35μl, 0.61 mmol) under an argon atmosphere at room temperature for 24 hr. The liquids were removed under reduced pressure, with purification by flash chromatography, eluting with 2:1 hexanes/ether, providing and trans acetate as an oil (133 mg, 72%). This oil (133 mg, 0.42 mmol) in methanol (2 ml) was treated with potassium hydroxide (89%, 52 mg 0.82 mmol) in water (0.3 ml) for 1 hr. The mixture was partitioned between ether and water, the ether was dried (potassium carbonate) and the solvent was removed in vacuo. Purification by flash chromatography, eluting with 1:1 hexanes/ether, provided the title compound as an oil (89 mg, 55.6%).

Provenance & Evidence