Lithium Hydroxide → HCID 54552529, compound

HRID 1489449Notes

Reaction equation

HRID 1489449 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[O:14][C@H:9]2[C:10]([O:12]C)=[O:11])=[CH:4][CH:3]=1.[OH-].[Li+]>CO.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[O:14][C@H:9]2[C:10]([OH:12])=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 53936350HCID 53936350, compound

Product 1

HCID 54552529HCID 54552529, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl (2R,3R)-3-(4-fluorophenyl)-2,3-epoxypropionate (206 mg, 1.05 mmol) dissolved in 5 ml of methanol was cooled by an ice bath, and a solution of lithium hydroxide (30 mg, 1.26 mmol) dissolved in water (3 ml) was added to the above solution. After the mixture was stirred at room temperature for 1.5 hours, the reaction mixture was concentrated. While cooling by an ice bath, a 5% citric acid aqueous solution was added to the residue obtained, and the mixture was extracted with chloroform. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. The solvent was removed to obtain (2R,3R)-3-(4-fluorophenyl)-2,3-epoxypropionic acid (which was unstable so that it could not be isolated nor purified).

Workup

  1. temperaturewas cooled by an ice bath
  2. additionwas added to the above solution
  3. concentrationthe reaction mixture was concentrated
  4. temperatureWhile cooling by an ice bath
  5. additiona 5% citric acid aqueous solution was added to the residue
  6. customobtained
  7. extractionthe mixture was extracted with chloroform
  8. washThe organic layer was washed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was removed

Sources & evidence

ORD record
ord-3be39e8ad3414de691782a735b130a2f
Source dataset
uspto-grants-1997_10
Patent number
US05677470

Reaction notes

Loading…