Potassium Carbonate → HCID 18790143, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 3-methanesulfonyloxy-2,2-dimethyl-7-phenylheptanoate (7.7 g, 23 mmol) and 4-methoxybenzenethiol (5.5 mL, 45 mmol) are dissolved in MeOH (40 mL) and potassium carbonate (4.8 g, 35 mmol) is added and the reaction is heated at 60° C. for 24 hours. The solvent is removed in vacuo and CH2Cl2 (100 mL) added and then washed with NaHCO3 (60 mL), 1 N HCl (60 mL) and brine (100 mL). The solvent is removed in vacuo and the residue purified by column chromatography (silica, 40% petroleum ether in CH2Cl2) to yield methyl 3-(4-methoxyphenylsulfanyl)-2,2-dimethyl-7-phenylheptanoate (2.1 g, 24%). 1H NMR (300 MHz, CDCl3) δ 7.36-7.33 (m, 2H), 7.29-7.12 (m, 5H), 6.82-6.79 (m, 2H), 3.79 (s, 3H), 3.55 (s, 3H), 3.18-3.15 (m, 1H), 2.60-2.53 (m, 2H), 1.85-1.73 (m, 1H), 1.57-1.40 (m, 5H), 1.26 (s, 3H), 1.20 (s, 3H); MS (FAB) m/e 386 (M+).

Provenance & Evidence