Phosphate → HCID 23595852, compound

HRID 890165Notes

Reaction equation

HRID 890165 reaction equation
[O:1]=[C:2]([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[CH3:10][Si:11]([CH3:16])([CH3:15])[CH2:12]CO.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][CH2:10][Si:11]([CH3:16])([CH3:15])[CH3:12])=[O:5]

Participants

6

Reactant 3

HCID 1061PhosphateHCID 180132-(Trimethylsilyl)ethanolHCID 121699Methyl 3-oxovalerate

Product 1

HCID 23595852HCID 23595852, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

1.26 ml (10.0 mmol) of methyl 3-oxovalerate, 2.87 ml (20.0 mmol) of 2-trimethylsilylethanol 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 obtained 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=10/1) 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=10/1)

Sources & evidence

ORD record
ord-a626ba788b164354998729add1927081
Source dataset
uspto-grants-2006_02
Patent number
US06995179B2

Reaction notes

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