Methanol → HCID 86755383, compound

Participants

Reaction Steps

A mixture of methyl 3-keto-7-phenylheptenoate (8 g, 34 mmol) and phosphorus pentachloride (14.1 g, 68 mmol) in hexane (60 mL) is heated under reflux for 2 hours. The solution is cooled in ice and methanol (5 mL) is added slowly. The mixture is stirred at room temperature for 10 minutes and is added to water and is extracted with hexane. The organic layer is dried over MgSO4 and the solvent is removed in vacuo. The residue is dissolved in dichloromethane (70 mL) and 17 mL of 2 M oxalyl chloride is added. The solution is stirred for 2 hours and the solvent is removed in vacuo. The residue is dissolved in dichloromethane and some methanol is added. After stirring for 30 minutes the solvent is removed in vacuo. The residue is chromatographed on silica gel (20:1 hexane:ethyl acetate) to give methyl (E)-3-chloro-7-phenyl-2-heptenoate (2.1 g, 25%) as the first component off the column and methyl (Z)-3-chloro-7-phenyl-2-heptenoate (1.4 g, 17%) as the second component off the column: methyl (E)-3-chloro-7-phenyl-2-heptenoate, 1H-NMR (300 MHz, CDCl3) δ (TMS) 1.58-1.69 (m, 4H), 2.57-2.60 (m, 2H), 2.92-3.04 (m, 2H), 3.68 (s, 3H), 6.06 (s, 1H), 7.12-7.22 (m, 3H), 7.22-7.45 (m, 2H); methyl (Z)-3-chloro-7-phenyl-2-heptenoate, 1H-NMR (300 MHz, CDCl3) δ (TMS) 1.58-1.78 (m, 4H), 2.38-2.50 (m, 2H), 2.57-2.62 (m, 2H), 3.72 (s, 3H), 6.00 (s, 1H), 7.12-7.27 (m, 3H), 7.27-7.38(m, 2H).

Provenance & Evidence