1-Butanol → 3-(2-Butoxy-6-trifluoromethyl-pyridin-3-yl)-acrylic acid

HRID 2265985Notes

Reaction equation

HRID 2265985 reaction equation
Cl[C:2]1[C:7]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[N:3]=1.[CH2:17]([OH:21])[CH2:18][CH2:19][CH3:20].[H-].[Na+]>CN(C=O)C.CCOC(C)=O.O>[CH2:17]([O:21][C:2]1[C:7]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[N:3]=1)[CH2:18][CH2:19][CH3:20]

Participants

7

Reactant 3

HCID 2631-ButanolHCID 24758Sodium hydrideHCID 723356323-(2-Chloro-6-trifluoromethyl-pyridin-3-yl)-acrylic acid

Product 1

HCID 687820263-(2-Butoxy-6-trifluoromethyl-pyridin-3-yl)-acrylic acidYield 92%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 3-(2-chloro-6-trifluoromethyl-pyridin-3-yl)-acrylic acid (40 mg, 0.158 mmol) and 1-butanol (0.029 ml, 0.316 mmol) in DMF (2 mL) was added NaH (19 mg, 0.47 mmol) at 0° C. The mixture was stirred for 12 hours at room temperature. The residue was diluted with EtOAc and water. The organic layer was washed with 1N HCl, saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude residue was column-chromatographed to give 3-(2-butoxy-6-trifluoromethyl-pyridin-3-yl)-acrylic acid (21 mg, 92%).

Workup

  1. washThe organic layer was washed with 1N HCl, saturated sodium bicarbonate and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was column-chromatographed

Sources & evidence

ORD record
ord-292e3781ccf84507a2354ad23adc851e
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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