Trimethylsulfonium iodide → HCID 90388258, compound

Participants

Reaction Steps

To a solution of compound 55 (40 mg, 0.144 mmol) in DSMO (3 mL) was added trimethylsulfonium iodide (204 mg, 1.0 mmol) and potassium tert-butoxide (112 mg, 1.0 mmol) at room temperature. After 3 h, water (20 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 30% EtOAc in hexanes) to give compound 56 (27 mg, 65%) as a white solid: mp 163-165° C.; [α]D25 +16.7 (c 0.12, CHCl3); 1H NMR (CDCl3) δ 3.64-3.60 (m, 1H), 2.90 (d, J=15.0 Hz, 1H), 2.61 (d, J=15.2 Hz, 1H), 0.86 (s, 3H); 13C NMR (CDCl3) δ 71.7, 70.5, 53.6, 47.1, 41.6, 40.7, 39.1, 38.6, 38.1, 36.2, 35.1, 35.0, 33.6, 33.0, 30.4, 29.8, 28.9, 25.6, 14.5; IR νmax 3379, 1443, 1375 cm−1. MS (FAB) for [C19H30O2]+: 290.2246. Found: 290.2243.

Provenance & Evidence