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

HRID 2265997Notes

Reaction equation

HRID 2265997 reaction equation
[CH3:1][CH:2]([OH:5])[CH2:3][CH3:4].[H-].[Na+].Cl[C:9]1[C:14]([CH:15]=[CH:16][C:17]([OH:19])=[O:18])=[CH:13][CH:12]=[C:11]([C:20]([F:23])([F:22])[F:21])[N:10]=1>CN(C=O)C.CCOC(C)=O>[CH:2]([O:5][C:9]1[C:14]([CH:15]=[CH:16][C:17]([OH:19])=[O:18])=[CH:13][CH:12]=[C:11]([C:20]([F:21])([F:23])[F:22])[N:10]=1)([CH2:3][CH3:4])[CH3:1]

Participants

6

Reactant 3

HCID 6568(+-)-2-ButanolHCID 24758Sodium hydrideHCID 723356323-(2-Chloro-6-trifluoromethyl-pyridin-3-yl)-acrylic acid

Product 1

HCID 687806843-(2-sec-Butoxy-6-trifluoromethyl-pyridin-3-yl)-acrylic acidYield 67.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Butanol (70.1 mg, 0.945 mmol) and sodium hydride (70 mg, 1.8 mmol) were added in DMF. The reaction mixture was stirred for 10 mins and then 3-(2-chloro-6-trifluoromethyl-pyridin-3-yl)-acrylic acid (67 mg, 0.266 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 (52 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-e8d9734e308d47bca8f2e719909c9614
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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