Dichloromethane → HCID 53240557, compound

Participants

Reaction Steps

To a suspension of compound 23 (5.00 g, 12.3 mmol) in dichloromethane (20 mL) at 0° C. under argon was slowly added boron tribromide (1.0 M in DCM, 12.5 mL, 12.5 mmol). The mixture was stirred for 60 h then concentrated. The residue was dissolved in ethyl acetate (50 mL), quenched with water (250 mL) and extracted with ethyl acetate (2×200 mL). The organic layer was washed with brine (2×250 mL) then dried (MgSO4) and concentrated to afford a brown foam. The crude product was purified by column chromatography on silica gel (hexanes:ethyl acetate, 2:1) to afford compound 57 (2.90 g, 60%) as a pale solid. 1H NMR (CDCl3): δ 7.00 (d, J=2.6 Hz, 1H), 6.54 (d, J=2.5 Hz, 1H), 6.20 (s, 1H), 3.79 (s, 3H), 3.36-3.16 (m, 3H), 2.27 (d, J=11.4 Hz, 1H), 1.72-1.00 (m, 10H), 1.38 (s, 3H), 0.95 (s, 3H), 0.86 (s, 3H), 0.83 (s, 3H). 13C NMR (CDCl3): δ 159.7, 157.0, 139.3, 127.8, 105.4, 102.4, 56.2, 56.1, 53.4, 46.3, 41.9, 39.8, 39.0, 38.1, 33.7, 33.5, 21.7, 19.2, 19.1, 18.8, 17.8, 17.7. MS m/z 393 (C22H32O4S+H+).

Provenance & Evidence