(Diethylamino)sulfur trifluoride → HCID 68109542, compound

Participants

Reaction Steps

DAST (0.4 mL, 3.20 mmol) was slowly added to a stirred solution of the product of step B (180 mg, 0.36 mmol) in anhydrous dichloromethane (12 mL) at 0° C. The resulting solution was allowed to warm to ambient temperature for 3 h then quenched by slow addition of aqueous sodium bicarbonate solution (10 mL). The organic layer was separated and the aqueous solution was further extracted with dichloromethane (2×20 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered, and the filtrate concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 9:1 to 7:3 hexanes/ethyl acetate) to give 6-chloro-1-(fluoromethyl)-2-(4-methoxybenzyl)-8-(phenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine (90 mg, 51%) as a colorless oil: 1H NMR (CDCl3, 300 MHz) δ 8.14 (d, J=1.2 Hz, 1H), 7.97-7.94 (m, 2H), 7.85 (d, J=1.5 Hz, 1H), 7.61-7.48 (m, 3H), 7.30-7.28 (m, 2H), 6.89-6.86 (m, 2H), 5.76-5.58 (m, 1H), 3.87 (s, 2H), 3.81 (s, 3H), 3.48-3.38 (m, 1H), 3.31-2.89 (m, 5H).

Provenance & Evidence