Hydrochloric Acid → HCID 10869545, compound

HRID 2210311Notes

Reaction equation

HRID 2210311 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]>[Ti](Cl)(Cl)(Cl)Cl.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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 12661DiketeneHCID 637511Cinnamaldehyde

Product 1

HCID 10869545HCID 10869545, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

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.

Workup

  1. stirringwere vigorously stirred at 0° C. over 30 minutes
  2. customto obtain a reaction mixture
  3. stirringvigorously stirred at 0° C. over 30 minutes
  4. stirringvigorously stirred at room temperature over 30 minutes
  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-78eea647302148558b091a0ce8a00388
Source dataset
uspto-grants-1995_10
Patent number
US05457225

Reaction notes

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