Potassium Hydroxide → HCID 13259209, compound

HRID 441791Notes

Reaction equation

HRID 441791 reaction equation
[CH3:1][CH:2]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:11]([F:21])[CH:10]=1)[C:3](=[O:8])[C:4]([O:6]C)=[O:5].[OH-].[K+]>CO>[CH3:1][CH:2]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:11]([F:21])[CH:10]=1)[C:3](=[O:8])[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 20323917HCID 20323917, compound

Product 1

HCID 13259209HCID 13259209, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 2.4 g of methyl 3-methyl-3-(2-fluoro-4-biphenylyl)-pyruvate in 40 ml of methanol was added a solution of 2.0 g of potassium hydroxide in 20 ml of methanol, and the resulting mixture was stirred at room temperature for 30 minutes. Subsequently, the methanol was removed from the mixture by distillation under reduced pressure. The residue was charged with water, and insoluble matter was removed therefrom by extraction with ethyl acetate. The extraction mother liquor was acidified with hydrochloric acid and then extracted with ethyl acetate. The ethyl acetate layer was successively washed with water and saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. The ethyl acetate was removed by distillation under reduced pressure to obtain 1.8 g of 3-methyl-3-(2-fluoro-4-biphenylyl)-pyruvic acid. The yield was 79%.

Workup

  1. customSubsequently, the methanol was removed from the mixture by distillation under reduced pressure
  2. additionThe residue was charged with water, and insoluble matter
  3. customwas removed
  4. extractionby extraction with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was successively washed with water and saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe ethyl acetate was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-82cdff6991a14af2a1aae09f0565fe01
Source dataset
uspto-grants-1977_08
Patent number
US04042617

Reaction notes

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