Hydrochloric Acid → HCID 10869545, compound

Participants

Reaction Conditions

Reaction Steps

In an atmosphere of argon, 9 ml of dichloromethane and 0.55 ml (5.0 mmol) of titanium tetrachloride were introduced in a schlenk tube, and cooled to 0° C. with stirring. To the dichloromethane solution, 0.68 g (5.2 mmol) of E-cinnamaldehyde and 0.77 ml (10 mmol) of diketene were added, and were vigorously stirred at 0° C. over 30 minutes to obtain a reaction mixture. To the reaction mixture, 2 ml of isopropyl alcohol was added, and vigorously stirred at 0° C. over 30 minutes. The reaction mixture was then added to a mixed solution of 25 ml of 1N HCl and 25 ml of dichloromethane, and vigorously stirred at room temperature over 30 minutes 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), a fraction corresponding to isopropyl E-5-hydroxy-3-oxo-7-phenyl-6-heptenoate was obtained in the same manner as Example 6. However, the fraction did not show the same peaks of NMR as those corresponding the isopropyl E-5-hydroxy-3-oxo-7-phenyl-6-heptenoate obtained in Example 6.

Provenance & Evidence