Hydrochloric Acid → HCID 10869545, compound

HRID 2210309Notes

Reaction equation

HRID 2210309 reaction equation
[CH:1](=[O:10])/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:11]=[C:12]1[O:16][C:14](=[O:15])[CH2:13]1.Cl.[CH:18]([OH:21])([CH3:20])[CH3:19]>ClCCl>[OH:10][CH:1](/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:11][C:12](=[O:16])[CH2:13][C:14]([O:21][CH:18]([CH3:20])[CH3:19])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 12661DiketeneHCID 637511Cinnamaldehyde

Product 1

HCID 10869545HCID 10869545, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-25 °C

Procedure

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).

Workup

  1. stirringwere vigorously stirred at -25° C. over 69 hours
  2. customto obtain a reaction mixture
  3. stirringwas vigorously stirred at -25° C. over 1 hour
  4. stirringvigorously stirred at room temperature over 2 hours
  5. customto give a solution
  6. extractionThe solution was extracted with three portions of 5 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)

Sources & evidence

ORD record
ord-038a9bc439a24e4280fdd24f8485da7f
Source dataset
uspto-grants-1995_10
Patent number
US05457225

Reaction notes

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