Isopropanol → HCID 90388261, compound

Participants

Reaction Steps

Jones reagent was added to a solution of compound 53 (115 mg, 0.42 mmol) in acetone (20 mL) at 0° C. until a brown-yellowish color persisted. After 10 min, 2-propanol (1.0 mL) was added to consume excess oxidant and then brine (50 mL) was added. The product was extracted into EtOAc (50 mL×3), and the combined extracts were dried, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel eluted with 25% EtOAc in hexanes) to give compound 54 (110 mg 4aR:4aS ratio 2.5:1) as a white solid: 1H NMR (CDCl3) δ 0.84 (s, 3H); 13C NMR (CDCl3) 4aR diastereomer δ 220.3, 212.2, 47.8, 45.6, 42.6, 39.8, 39.0, 38.5, 38.2, 38.1, 36.3, 35.4, 30.7, 28.5, 28.4, 27.1, 23.9, 13.5.

Provenance & Evidence