Hydrogen Peroxide → HCID 90388298, compound

Participants

Reaction Steps

To a solution of compound 38 (570 mg, 2.1 mmoL) in THF (20 mL) was added K-selectride (2.6 mmol, 2.6 mL, 1.0 M in THF) at −78° C. After 3 h, aqueous 10% NaOH (30 mL) and 30% H2O2 (20 mL) were added at −78° C. After addition, the reaction was warmed up to room temperature for 1 h. 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 30% EtOAc in hexanes) to give compound 39 (456 mg, 80%) as a white solid: mp 143-145° C., [α]D25 −41.0 (c 0.19, CHCl3); 1H NMR (CDCl3) δ 3.95-3.90 (m, 1H), 0.75 (s, 3H); 13C NMR (CDCl3) δ 220.8, 65.8, 48.1, 47.5, 46.9, 45.4, 40.2, 39.1, 37.8, 35.8, 35.4, 33.8, 33.7, 32.5, 28.1, 23.8, 23.1, 13.3; IR νmax 3422, 1737 cm−1; Anal. Calcd for (C18H25O2): C, 78.21; H, 10.21. Found: C, 78.29; H, 10.43.

Provenance & Evidence