Acetone → 2-Butenoic acid, 2-fluoro-3-methyl-, ethyl ester

HRID 1728050Notes

Reaction equation

HRID 1728050 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6](P(OCC)(OCC)=O)[F:7])=[O:5].[H-].[Na+].[CH3:18][C:19]([CH3:21])=O>C(COC)OC.O>[CH2:2]([O:3][C:4](=[O:5])[C:6]([F:7])=[C:19]([CH3:21])[CH3:18])[CH3:1]

Participants

6

Reactant 3

HCID 180AcetoneHCID 24758Sodium hydrideHCID 2734865Triethyl 2-fluoro-2-phosphonoacetate

Product 1

HCID 103969592-Butenoic acid, 2-fluoro-3-methyl-, ethyl esterYield 74.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Triethyl 2-fluoro-2-phosphonoacetate (20 g, 82.6 mmol) (Aldrich) was added dropwise to a stirred solution of sodium hydride (3.6 g, 90.8 mmol) in dimethoxyethane (100 mL) at 0° C. After stirring at room temperature for 20 min, acetone (4.78 g, 82.6 mmol) was added and the reaction mixture was refluxed for overnight. The two phase mixture was cooled, diluted with water and extracted with ether. The combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified with chromatography (Hexanes) to give 2-fluoro-3-methyl-but-2-enoic acid ethyl ester as colorless oil (Yield: 9.0 g, 61.6%).

Workup

  1. temperaturethe reaction mixture was refluxed for overnight
  2. temperatureThe two phase mixture was cooled
  3. extractionextracted with ether
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified with chromatography (Hexanes)

Sources & evidence

ORD record
ord-3dc8f25cc26740bfb920322f555e79a2
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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