3-Phenylprop-2-En-1-Ol → (3-Phenyl-2-propene-1-yl) 4,4-dimethoxy-3-oxobutyrate

HRID 890148Notes

Reaction equation

HRID 890148 reaction equation
[CH3:1][O:2][CH:3]([O:12][CH3:13])[C:4](=[O:11])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].C(O)C=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.P([O-])([O-])([O-])=O>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[CH3:1][O:2][CH:3]([O:12][CH3:13])[C:4](=[O:11])[CH2:5][C:6]([O:8][CH2:9][CH:10]=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:7]

Participants

6

Reactant 3

HCID 3083-Phenylprop-2-En-1-OlHCID 1061PhosphateHCID 248327Ethyl 4,4-dimethoxy-3-oxobutanoate

Product 1

HCID 53702825(3-Phenyl-2-propene-1-yl) 4,4-dimethoxy-3-oxobutyrate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

2.68 g (14.1 mmol) of ethyl 4,4-dimethoxy-3-oxobutyrate, 5.14 ml (40.0 mmol) of cinnamyl alcohol and 244 mg (2.0 mmol) of 4-dimethylaminopyridine were heated under reflux in 40 ml of toluene for two nights. A phosphate buffer solution was added to the reaction liquid. After the extraction with ethyl acetate, the organic layer was washed with a saturated aqueous salt solution and then dried over anhydrous sodium sulfate. The solvent was distilled 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 a saturated aqueous salt solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled under reduced pressure
  5. customthe residue was purified by the silica gel chromatography (hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-129c43881bba449a97daf6ee863e90ff
Source dataset
uspto-grants-2006_02
Patent number
US06995179B2

Reaction notes

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