Water → HCID 18693929, compound

HRID 1870834Notes

Reaction equation

HRID 1870834 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([OH:15])([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:4][C:3]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[H-].[Na+].I[CH2:25][CH3:26].O>CN(C)C=O.C(O)C>[CH2:25]([O:15][C:8]([C:6]1[CH:5]=[CH:4][C:3]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[C:2]([F:1])[CH:7]=1)([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH3:26]

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 13423264HCID 13423264, compound

Product 1

HCID 18693929HCID 18693929, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, ethyl 2-(2-fluoro-biphenyl-4-yl)-2-hydroxy-propionate (Japanese Patent Unexamined Publication No. 52-105,144) (15.0 g) was dissolved in N,N-dimethylformamide (300 ml) and then sodium hydride (4.16 g, 60% oily) was added under ice-cooling, after which the resulting mixture was stirred for one hour. Subsequently, iodoethane (10.4 ml) was added and the resulting mixture was stirred for 12 hours. To the reaction mixture were added a small amount of water and ethanol, and thereafter, the solvent was removed by azeotropic distillation using toluene. To the residue was added ethyl acetate and the resulting mixture was neutralized with a saturated aqueous sodium bicarbonate solution and then subjected to extraction with ethyl acetate. The organic layer was dried over sodium sulfate and then concentrated under reduced pressure to obtain ethyl 2-ethoxy2-(2-fluoro-biphenyl-4-yl)-propionate.

Workup

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred for 12 hours
  3. customthe solvent was removed by azeotropic distillation
  4. additionTo the residue was added ethyl acetate
  5. extractionsubjected to extraction with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-85068461ede84616b37dd511e5188046
Source dataset
uspto-grants-2000_08
Patent number
US06100260

Reaction notes

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