Water → HCID 18693525, compound

HRID 1870833Notes

Reaction equation

HRID 1870833 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:12])[C:9]([OH:11])=O)[CH:5]=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H-].[Na+].I[CH3:22].O.CN(C)[CH:26]=[O:27]>>[F:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:22])([CH3:12])[C:9]([O:27][CH3:26])=[O:11])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 5

HCID 962WaterHCID 3394FlurbiprofenHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydride

Product 1

HCID 18693525HCID 18693525, compound

Procedure

Under a nitrogen atmosphere, 2-(2-fluoro-biphenyl-4-yl)-propionic acid (15.0 g) was dissolved in N,N-dimethylformamide (150 ml) and then sodium hydride (6.14 g, 60% oily) was added, after which the resulting mixture was stirred for one hour. Subsequently, iodomethane (9.5 ml) was added and the mixture was stirred for 12 hours. A small amount of water was added to the reaction mixture and the resulting mixture was then subjected to extraction with ethyl acetate. The organic layer was dried over sodium sulfate and then concentrated under reduced pressure. The residue was purified by a recrystallization method from hexane, to obtain methyl 2-(2-fluoro-biphenyl-4-yl)-2-methyl-propionate (14.2 g).

Workup

  1. stirringthe mixture was stirred for 12 hours
  2. extractionthe resulting mixture was then subjected to extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by a recrystallization method from hexane

Sources & evidence

ORD record
ord-cb12207fc01f461ca1266e8c3a7ba9e9
Source dataset
uspto-grants-2000_08
Patent number
US06100260

Reaction notes

Loading…