Isopropanol → HCID 90388634, compound

Participants

Reaction Steps

Jones reagent was added to a solution of compound 37 (605 mg, 2.2 mmol) in acetone (40 mL) at 0° C. until a brown-yellowish color persisted. After 10 min, 2-propanol (1.0 mL) was added to consume excess oxidant. Brine (50 mL) was added and the product extracted into EtOAc (50 mL×3). The combined extracts were dried, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel eluted with 20% EtOAc in hexanes) to give compound 38 (580 mg, 96%) as a white solid: [α]D25 −13.1 (c 0.145, CHCl3); 1H NMR (CDCl3) δ 0.81 (s, 3H); 13C NMR (CDCl3) δ 220.1, 211.0, 48.2, 47.8, 47.6, 45.6, 45.4, 43.5, 40.9, 38.9, 37.6, 3.54, 34.0, 33.4, 29.9, 28.7, 23.8, 13.4; IR νmax 1716, 1715 cm−1.

Provenance & Evidence