Acetic Acid → HCID 20323917, compound

HRID 441790Notes

Reaction equation

HRID 441790 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][CH:19]=[CH:18][CH:17]=2)=[C:12]([F:22])[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:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([F:22])[CH:11]=1)[C:3](=[O:2])[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5360545SodiumHCID 20323921HCID 20323921, compound

Product 1

HCID 20323917HCID 20323917, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 1.1 g of metallic sodium in 100 ml of anhydrous methanol was added a solution of 12.2 g of methyl 2-hydroxy-3-(2-fluoro-4-biphenylyl)-3-butenoate in 40 ml of anhydrous methanol, and the resulting mixture was refluxed for 20 minutes and then cooled. The reaction liquid was charged with 10 ml of glacial acetic acid, and the methanol was removed therefrom by distillation at a low temperature and under reduced pressure. The residue was charged with ethyl acetate and water, thereby effecting ethyl acetate extraction. The ethyl acetate layer was successively washed with water, aqueous sodium bicarbonate solution and water, and then dried over anhydrous magnesium sulfate. Thereafter, the ethyl acetate was removed by distillation under reduced pressure to obtain 9.0 g of methyl 3-methyl-3-(2-fluoro-4-biphenylyl)-pyruvate. The yield was 73%.

Workup

  1. temperaturethe resulting mixture was refluxed for 20 minutes
  2. temperaturecooled
  3. customThe reaction liquid
  4. customthe methanol was removed
  5. distillationby distillation at a low temperature
  6. additionThe residue was charged with 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. dry with materialdried over anhydrous magnesium sulfate
  10. customThereafter, the ethyl acetate was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-b5690aad40f54c4fb13932b230bc0523
Source dataset
uspto-grants-1977_08
Patent number
US04042617

Reaction notes

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