Sodium Bicarbonate → HCID 10954146, compound

HRID 2166936Notes

Reaction equation

HRID 2166936 reaction equation
[C:1]1([CH:7]([F:15])[C:8](=[O:14])[C:9]([O:11]CC)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)(O)[O-].[Na+]>C(O)(C)C>[C:1]1([CH:7]([F:15])[C:8](=[O:14])[C:9]([OH:11])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 11095876HCID 11095876, compound

Product 1

HCID 10954146HCID 10954146, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To the crude product of ethyl 3-phenyl-3-fluoropyruvate (10.6 g) obtained in Example 1, a 50% aqueous solution of isopropanol (300 ml) is added, and sodium bicarbonate (9.0 g) is added thereto. The mixture is heated gradually while stirring, and hydrolysis is effected at 50° C. for 15 hours. Thereafter, water-insoluble substances are extracted with ethyl acetate (70 ml each for three times). Then, the water layer is admixed with ethyl acetate (200 ml) and made acidic (pH, 1.0-2.0) with 1 N hydrochloric acid under ice cooling. The ethyl acetate layer is dried over magnesium sulfate and distilled under reduced pressure to give 3-phenyl-3-fluoropyruvic acid (6.3 g) as an oil.

Workup

  1. temperatureThe mixture is heated gradually
  2. customhydrolysis
  3. extractionThereafter, water-insoluble substances are extracted with ethyl acetate (70 ml each for three times)
  4. dry with materialThe ethyl acetate layer is dried over magnesium sulfate
  5. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-bb6b6d540dd94bcfa651db772287b1a0
Source dataset
uspto-grants-1983_06
Patent number
US04390702

Reaction notes

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