3-Phenylprop-2-En-1-Ol → HCID 53744919, compound

HRID 890156Notes

Reaction equation

HRID 890156 reaction equation
[O:1]=[C:2]([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5].C(O)[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.P([O-])([O-])([O-])=O>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[O:1]=[C:2]([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH2:7][CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:5]

Participants

6

Reactant 3

HCID 3083-Phenylprop-2-En-1-OlHCID 1061PhosphateHCID 121699Methyl 3-oxovalerate

Product 1

HCID 53744919HCID 53744919, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

1.26 ml (10.0 mmol) of methyl 3-oxovalerate, 2.57 ml (20.0 mmol) of cinnamyl alcohol and 122 mg (1.0 mmol) of 4-dimethylaminopyridine were heated under reflux in 20 ml of toluene overnight. A phosphate buffer solution was added to the reaction liquid. After the extraction with ethyl acetate, the organic layer was washed with saturated aqueous salt solution and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by the silica gel chromatography (hexane/ethyl acetate=9/1) to obtain the title compound.

Workup

  1. extractionAfter the extraction with ethyl acetate
  2. washthe organic layer was washed with saturated aqueous salt solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by the silica gel chromatography (hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-8a32f5a4dd4243ad846119512f668d31
Source dataset
uspto-grants-2006_02
Patent number
US06995179B2

Reaction notes

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