Toluene → HCID 22458367, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of bis(2,2,2-trifluoromethyl)(methoxy carbonylmethyl)phosphonate (0.38 ml, 1.8 mmol) in 2.5 ml anhydrous tetrahydrofuran was added a solution of 18-Crown-6 (1.9 g, 7.5 mmol) in 2.5 ml anhydrous tetrahydrofuran. The reaction mixture was cooled to −78° C. under argon to which was added a solution of 0.5M bis(trimethylsilyl)amide in toluene (3.6 ml, 1.8 mmol). The reaction was stirred at −78° C. for 15 minutes to which was added a solution of 3-(2-methylpropanoyl)benzenecarbonitrile in 2.5 ml anhydrous tetrahydrofuran. The reaction was allowed to warm to room temperature and stirred for 48 hours. The reaction was quenched by the addition of 20 ml of a saturated ammonium chloride solution followed by extraction with 2×25 ml diethyl ether. Combined organic layers were washed with 2×25 ml water, 2×25 ml saturated brine solution, dried over magnesium sulfate, filtered and concentrated to give a 9:1 mixture of methyl (2Z)-3-(3-cyanophenyl)-4-methylpent-2-enoate and methyl (2E)-3-(3-cyanophenyl)-4-methylpent-2-enoate (420 mg, 120%) as a clear oil which was sufficiently pure to use without further purification. ES-MS (M+H+): 230.1.

Provenance & Evidence