Hydrochloric Acid → HCID 10869545, compound

Participants

Reaction Conditions

Reaction Steps

In an atmosphere of argon, 10 ml of dichloromethane and 2.5 ml (5.0 mmol) of the above titanium dichlorodiiso-propoxide-dichloromethane solution were placed in a schlenk tube, and cooled to -25° C. with stirring. To the dichloromethane solution, 0.656 g (5.0 mmol) of E-cinnamaldehyde and 0.77 ml (10 mmol) of diketene were added, and were vigorously stirred at -25° C. over 69 hours to obtain a reaction mixture. To the reaction mixture, 1.5 ml of isopropyl alcohol was added, and was vigorously stirred at -25° C. over 1 hour. The reaction mixture was added to a mixed solution of 25 ml of 1N HCl and 25 ml of dichloromethane, and vigorously stirred at room temperature over 2 hours to give a solution. The solution was extracted with three portions of 5 ml of dichloromethane. The dichloromethane portions were combined, and dried by adding anhydrous magnesium sulfate. The solvent of the solution was removed by distillation in vacuo to obtain a concentrated solution. The concentrated solution was placed on a silica gel column and eluted with a mixture of hexane and ethyl acetate (hexane:ethyl acetate=7:3) to give 0.188 g of isopropyl E-5-hydroxy-3-oxo-7-phenyl-6-heptenoate (yield: 14% based on the amount of E-cinnamaldehyde).

Provenance & Evidence