Acetic Acid → HCID 12264293, compound

HRID 441788Notes

Reaction equation

HRID 441788 reaction equation
[Na].[OH:2][CH:3]([C:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)=[CH2:9])[C:4]([O:6][CH3:7])=[O:5].C(O)(=O)C>CO>[CH3:9][CH:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)=[CH:12][CH:11]=1)[C:3](=[O:2])[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5360545SodiumHCID 12264287HCID 12264287, compound

Product 1

HCID 12264293HCID 12264293, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 0.55 g of metallic sodium in 50 ml of anhydrous methanol was added a solution of 6.1 g of methyl 2-hydroxy-3-(4'-fluoro-4-biphenylyl)-3-butenoate in 20 ml of anhydrous methanol. The resulting mixture was refluxed for 20 minutes and then cooled, and the reaction liquid was charged with 5 ml of glacial acetic acid. The mixture was distilled at a low temperature and under reduced pressure to remove the methanol therefrom. To the residue were added ethyl acetate and water, thereby effecting ethyl acetate extraction. The ethyl acetate layer was successively washed with water, aqueous sodium bicarbonate solution and water. The ethyl acetate was removed by distillation under reduced pressure to obtain crude crystals. 5.4 Grams of the crude crystals was recrystallized from ethanol to obtain 4.6 g of methyl 3-methyl-3-(4'-fluoro-4-biphenylyl)-pyruvate, m.p. 100.0°-101.6° C. The yield was 75%.

Workup

  1. temperatureThe resulting mixture was refluxed for 20 minutes
  2. temperaturecooled
  3. customthe reaction liquid
  4. distillationThe mixture was distilled at a low temperature and under reduced pressure
  5. customto remove the methanol
  6. additionTo the residue were added ethyl acetate and water
  7. extractioneffecting ethyl acetate extraction
  8. washThe ethyl acetate layer was successively washed with water, aqueous sodium bicarbonate solution and water
  9. customThe ethyl acetate was removed by distillation under reduced pressure
  10. customto obtain crude crystals
  11. custom5.4 Grams of the crude crystals was recrystallized from ethanol

Sources & evidence

ORD record
ord-5d2324490c3745f098e9b22764910627
Source dataset
uspto-grants-1977_08
Patent number
US04042617

Reaction notes

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