Hydrochloric Acid → HCID 10869545, compound

Temperature

0 °C

In an atmosphere of argon, 10 ml of dichloromethane and 1.92 g (7.5 mmol) of titanium monochlorotriisopropoxide were placed in a schlenk tube, and cooled to 0° C. with stirring. To the dichloromethane solution, 0.99 g (7.5 mmol) of E-cinnamaldehyde and 1.16 ml (15 mmol) of diketene were added, and vigorously stirred at 0° C. over 21 hours to obtain a reaction mixture. To the reaction mixture, 0.6 ml of isopropyl alcohol was added, and vigorously stirred at 0° C. over 1 hour. The reaction mixture was added to a mixed solution of 50 ml of 1N HCl and 50 ml of diethyl ether, and vigorously stirred at room temperature over 15 hours to give a solution. The solution was extracted with three portions of 10 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 0.64 g of isopropyl E-5-hydroxy-3-oxo-7-phenyl-6-heptenoate (yield: 31% based on the amount of E-cinnamaldehyde).

1. stirringvigorously stirred at 0° C. over 21 hours
2. customto obtain a reaction mixture
3. stirringvigorously stirred at 0° C. over 1 hour
4. stirringvigorously stirred at room temperature over 15 hours
5. customto give a solution
6. extractionThe solution was extracted with three portions of 10 ml of dichloromethane
7. customdried
8. additionby adding anhydrous magnesium sulfate
9. customThe solvent of the solution was removed by distillation in vacuo
10. customto obtain a concentrated solution
11. washeluted with a mixture of hexane and ethyl acetate (hexane:ethyl acetate=7:3)

ORD record

ord-8dba002a387949d48b3a00930c786875

Source dataset

uspto-grants-1995_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05457225