Potassium Carbonate → HCID 86755385, compound

Participants

Reaction Steps

A mixture of methyl (E)-3-chloro-7-phenyl-2-heptenoate (1.3 g, 5.1 mmol), 3,4-dimethoxythiophenol (0.86 g, 5.1 mmol) and potassium carbonate (0.7 g, 5.1 mmol) in methanol (50 mL) is heated under reflux for 3 hours. The mixture is filtered and the filtrate is poured into water and is extracted with ether. The organic layer is washed with water and is dried over MgSO4. The solvent is removed in vacuo and the residue is chromatographed (4:1 hexane:ethyl acetate) to obtain methyl (E)-3-[(3,4-dimethoxyphenyl)thio]-7-phenyl-2-heptenoate (0.6 g, 31% ). A small amount is recrystallized from hexane to give m.p. 53-5° C. Anal.(C22H26O4S) C, H: 1H-NMR (300 MHz, CDCl3) δ (TMS) 1.68-1.82 (m, 4H), 2.60-2.70 (m, 2H) 2.80-2.92 (m, 2H), 3.57 (s, 3H), 3.86 (s,3H), 3.90 (s, 3H), 5.12 (s, 1H), 6.82-6.92 (m, 2H), 6.98-7.08 (m, 1H), 7.13-7.31 (m, 5H); MS (EI) m/e 386 (M+).

Provenance & Evidence