Hydrogen Peroxide → HCID 78323392, compound

Participants

Reaction Steps

To a solution of compound 21 (460 mg, 1.6 mmoL) in THF (20 mL) was added K-selectride (2.0 mmol, 2.0 mL, 1.0 M) at −78° C. After 3 h, 10% aqueous NaOH (30 mL) and 30% H2O2 (20 mL) were added at −78° C. The reaction was then warmed to room temperature for 1 h. The product was 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 30% EtOAc in hexanes) to give compound 22 (294 mg, 64%) as a white solid: mp 179-181° C., [α]D25 +46.9 (c 0.16, CHCl3); 1H NMR (CDCl3) δ 4.05 (s, br, 1H), 0.85 (s, 3H), 0.79 (s, 3H); 13C NMR (CDCl3) δ 221.1, 66.4, 54.6, 47.8, 45.8, 39.8, 39.1, 36.4, 35.7, 34.8, 32.0, 31.8, 28.8, 28.7, 24.1, 24.0, 13.6, 11.2; IR νmax 3434, 1736 cm−1. Anal. Calcd for (C19H30O2): C, 78.57; H, 10.41. Found: C, 78.45; H, 10.28.

Provenance & Evidence