Pyridine → Methyl 4-fluoro-3-oxobutanoate

HRID 364966Notes

Reaction equation

HRID 364966 reaction equation
[F:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][C:7]1(C)[O:12]C(=O)C[C:9](=O)[O:8]1.N1C=CC=CC=1>C(Cl)Cl>[F:1][CH2:2][C:3](=[O:4])[CH2:6][C:7]([O:8][CH3:9])=[O:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 9663Fluoroacetyl chlorideHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 14170515Methyl 4-fluoro-3-oxobutanoateYield 65.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Fluoroacetyl chloride (7.1 g, 73 mmoles) was added dropwise to a stirred solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (10.65 g, 74 mmoles) and pyridine (16.85 ml, 210 mmoles) in methylene chloride (75 ml) keeping the temperature below 10°. After stirring for 16 hours at room temperature the solution was diluted with methylene chloride (100 ml and then washed with 1N hydrochloric acid (200 ml) and water (100 ml). The organic extract was dried (Na2SO4) and the solvent removed in vacuo. The residue was dissolved in methanol (150 ml) and the solution heated at reflux for 2.5 hours. Removal of the solvent followed by distillation at 60°-80° (bath temp)/14 mm Hg gave methyl 4-fluoro-3-oxobutanoate (6.4 g).

Workup

  1. customthe temperature below 10°
  2. washwashed with 1N hydrochloric acid (200 ml) and water (100 ml)
  3. extractionThe organic extract
  4. dry with materialwas dried (Na2SO4)
  5. customthe solvent removed in vacuo
  6. dissolutionThe residue was dissolved in methanol (150 ml)
  7. temperaturethe solution heated
  8. temperatureat reflux for 2.5 hours
  9. customRemoval of the solvent
  10. distillationfollowed by distillation at 60°-80° (bath temp)/14 mm Hg

Sources & evidence

ORD record
ord-b4bf3f3a248249e68c4b8e8a59d0546e
Source dataset
uspto-grants-1986_08
Patent number
US04607041

Reaction notes

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