Water → HCID 90388236, compound

Participants

Reaction Steps

To a solution of compound 46 (200 mg, 0.72 mmol) in dry dichloromethane (10 mL) was added N,N-diisopropylethylamine (260 mg, 2.0 mmol) and chloromethyl methyl ether (241 mg, 3.0 mmol) at room temperature. After 16 h, water (30 mL) was added and the product extracted into dichloromethane (50 mL×3). The combined extracts were dried, filtered and concentrated. The residue was purified by flash column chromatography (silica gel eluted with 10% EtOAc in hexanes) to give compound 47 (230 mg, 100%) as a white solid: [α]D25 −40.0 (c 0.20, CHCl3); 1H NMR (CDCl3) δ 4.60 (s, 2H), 3.83-3.82 (m, 1H), 3.31 (s, 3H), 0.81 (s, 3H); 13C NMR (CDCl3) δ 220.9, 94.5, 71.2, 55.0, 48.3, 47.7, 46.9, 45.6, 39.3, 38.1, 37.9, 36.6, 35.6, 33.9, 30.2, 28.3, 24.0, 2.39, 13.5; IR νmax 1740 cm−1.

Provenance & Evidence