Pyridine → 4-(2'-Carboxy-2'-methylpropylmercapto)phenyl 2-phenylbutyrate

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A solution of 2-phenylbutyryl chloride (1.19 g, 6.5 mmol) in 5 mL of THF was added to a stirred solution of 2,2-dimethyl-3-(4'-hydroxyphenylthio)-propionic acid (1.36 g, 6.0 mmol) and pyridine (1.03 g, 13.0 mmol) in 10 mL of THF under N2. After 6 days, 30 mL of ether was added and the reaction mixture filtered into a separatory funnel. The organic layer was washed with 0.5N HCl (2×15 mL), saturated NaCl (15 mL), 1:9 saturated NaHCO3 /H2O (2×15 mL), saturated NaCl (15 mL) and dried over anhydrous MgSO4. Filtration and evaporation provided 1.96 g (88%) of the desired ester. 1H NMR (CDCl3) δ0.974 (t, 3H, J=7.2 Hz), 1.27 (s, 6H), 1.82-1.96 (m, 1H), 2.13-2.28 (m, 1H), 3.13 (s, 2H), 3.67 (t, 1H, J=7.5 Hz), 6.90 (d, 2H, J=8.7 Hz), 7.30-7.38 (ArH, 7H), 11.9 (br s, --OH); 13C NMR (CDCl3) δ11.84, 24.30, 26.45, 43.73, 44.95, 53.27, 122.06, 127.58, 128.01, 128.88, 131.66, 134.27, 138.58, 149.65, 172.75, 183.22.

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