4-(Chlorosulfonyl)-2-hydroxybenzoic acid → 4-[4-(2-Benzyl-4,5-dimethyl-furan-3-carbonyl)-2,6-diethyl-phenoxysulfonyl]-2-hydroxy-benzoic Acid

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Reaction Steps

The title compound was prepared according to the procedure in Example 4 using (2-benzyl-4,5-dimethyl-furan-3-yl)-(3,5-diethyl-4-hydroxy-phenyl)-methanone (0.5 g, 1.38 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (0.65 g, 2.74 mmol). Purification on 2% H3PO4/MeOH treated silica gel, eluting with 10% EtOAc/hexane gave 0.251 g (32%) of the title compound as an off white solid, mp 143-147° C. 1H NMR (DMSO-d6) δ 1.01 (t, 6H), 1.84 (s, 3H), 2.20 (s, 3H), 2.51 (q, 4H, with DMSO peak), 3.81 (s, 2H), 7.01 (d, 2H), 7.16-7.20 (m, 1H), 7.23-7.27 (m, 2H), 7.45 (s, 2H), 7.49-7.53 (m, 2H), 8.06 (d, 1H). mass spectrum (−ESI), m/z 561 (M−H). Anal. Calcd. for C31H30O8S: C, 66.18; H, 5.37; N, 0.00. Found: C, 65.80; H, 5.50; N, 0.22.

Provenance & Evidence