2-Chlorobenzenesulfonyl chloride → HCID 57122770, compound

Participants

Reaction Steps

To all of 2-[3-(3-hydroxy-5-methoxyphenyl)propyl]-1,3-dioxane, as prepared in step d, in dichloromethane (2 mL) containing 500 μL of N,N-diisopropylethylamine was added 166 mg (0.79 mmol) of 2-chlorobenzenesulfonyl chloride. After stirring at ambient temperature for 30 min, 5 mg of N,N-dimethylaminopyridine was added and the reaction mixture was stirred for an additional 30 min. The reaction mixture was quenched with 10% aqueous citric acid, extracted into diethyl ether, dried (MgSO4), concentrated, and purified by flash chromatography (dichloromethane/diethyl ether (100:0 to 95:5)) to give 180 mg (77% yield from 2-[3-(3-hydroxy-5-methoxyphenyl)-3-propenyl]-1,3-dioxane) of the title compound. 1H-NMR (300 MHz, CDCl3) δ 7.84 (dd, 1 H, J 1.5, 8 Hz), 7.53-7.63 (m, 2 H), 7.33-7.39 (m, 1 H), 6.59 (t, 1 H, J =2 Hz), 6.50 (m, 2 H), 4.48 (t, 1 H, J=5 Hz), 4.06-4.11 (m, 2 H), 3.70 (s,3 H), 3.71-3.79(m,2 H), 2.49 (t, 2 H, J=5 Hz), 1.98-2.14 (m, 1 H), 1.25-1.6 (m, 5 H). Mass spectrum (MALDI-TOF, gentisic acid matrix) calcd. for C20H23ClO6S: 449.1 (M+Na). Found: 449.1.

Provenance & Evidence