Phenol → 3-(2-Phenoxy-6-trifluoromethyl-pyridin-3-yl)-acrylic acid

HRID 2265999Notes

Reaction equation

HRID 2265999 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:11]1[C:16]([CH:17]=[CH:18][C:19]([OH:21])=[O:20])=[CH:15][CH:14]=[C:13]([C:22]([F:25])([F:24])[F:23])[N:12]=1>CN(C=O)C.CCOC(C)=O>[O:7]([C:11]1[C:16]([CH:17]=[CH:18][C:19]([OH:21])=[O:20])=[CH:15][CH:14]=[C:13]([C:22]([F:23])([F:25])[F:24])[N:12]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 723356323-(2-Chloro-6-trifluoromethyl-pyridin-3-yl)-acrylic acid

Product 1

HCID 687833273-(2-Phenoxy-6-trifluoromethyl-pyridin-3-yl)-acrylic acidYield 18%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Phenol (57 mg, 0.60 mmol) and sodium hydride (32 mg, 0.8 mmol) were added in DMF (15 mL). The reaction mixture was stirred for 10 mins and then 3-(2-chloro-6-trifluoromethyl-pyridin-3-yl)-acrylic acid (70 mg, 0.27 mmol) was added into the reaction mixture. The reaction mixture was diluted with EtOAc, and washed with water and brine. The organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. The resulting residue was purified by column chromatography (Hex EtOAc=1/1) to give the title product (15 mg).

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by column chromatography (Hex EtOAc=1/1)

Sources & evidence

ORD record
ord-f539b22a64f7474da7f14386e0113d1b
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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