Water → Ethyl 2-acetyl-5,5-dimethyl-4-oxohexanoate

HRID 1674126Notes

Reaction equation

HRID 1674126 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH:5]=[C:6]([O-:8])[CH3:7])[CH3:2].[Na+].Br[CH2:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15].C(OCC)(=O)C.O>CN(C)C=O>[C:6]([CH:5]([CH2:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[C:4]([O:3][CH2:1][CH3:2])=[O:9])(=[O:8])[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21642BromopinacoloneHCID 74084341HCID 74084341, compound

Product 1

HCID 11775940Ethyl 2-acetyl-5,5-dimethyl-4-oxohexanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of sodium 4-ethoxy-4-oxobut-2-en-2-olate (1.50 g) in N,N-dimethylformamide (50 mL) was added 1-bromo-3,3-dimethylbutan-2-one (2.0 mL), and the mixture was stirred at room temperature for 1 hr. Ethyl acetate and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography to give the title compound as a pale-yellow viscous substance (1.51 g, 53%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bb566a9f33d44ba58a8cae97c84d1736
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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