Hydrochloric Acid → HCID 86755386, compound

Participants

Reaction Steps

A mixture of methyl (Z)-3-chloro-7-phenyl-2-heptenoate (0.7 g, 2.77 mmol), 3,4-dimethoxythiophenol (0.47 g, 2.77 mmol) and potassium carbonate (0.38 g, 2.77 mmol) in methanol (30 mL) is heated under reflux for 3 hours. The mixture is added to aqueous HCl 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 on silica gel (4:1 hexane:ethyl acetate) to produce methyl (Z)-3-[(3,4-dimethoxyphenyl)thio]-7-phenyl-2-heptenoate as an oil (0.8 g, 75% ): 1H-NMR (300 MHz, CDCl3) δ (TMS) 1.30-1.53 (m, 3H), 1.62-1.76 (m, 1H), 2.03-2.18 (m, 2H), 2.38-2.48 (m, 1H), 2.64-2.74 (m, 1H), 3.72 (s, 3H), 3.78-3.90 (m, 6H), 5.78 (s, 1H), 6.72-6.82 (m, 1H), 6.92-7.00 (m, 1H), 7.05-7.10 (m, 1H), 7.20-7.38 (m, 5H).

Provenance & Evidence