Lithium Hydroxide → HCID 68782564, compound

HRID 2266029Notes

Reaction equation

HRID 2266029 reaction equation
[CH2:1]([C:6]1[C:11]([CH:12]=[CH:13][C:14]([O:16]C)=[O:15])=[CH:10][CH:9]=[C:8]([C:18]([F:21])([F:20])[F:19])[N:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[Li+].[OH-]>C1COCC1.O>[CH2:1]([C:6]1[C:11]([CH:12]=[CH:13][C:14]([OH:16])=[O:15])=[CH:10][CH:9]=[C:8]([C:18]([F:21])([F:19])[F:20])[N:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86625538HCID 86625538, compound

Product 1

HCID 68782564HCID 68782564, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of compound 3-(2-pentyl-6-trifluoromethyl-pyridin-3-yl)-acrylic acid, methyl ester (366 mg, 1.22 mmol) in THF (3 ml) was added a solution of 1 N-LiOH (3.0 ml), and the mixture was stirred for 3 hours at room temperature. The resulting residue was dissolved in H2O and then washed with EtOAc, acidified with 1N HCl to pH 1˜2. The solution was extracted three times with methylene chloride and then dried over anhyd. MgSO4 and concentrated in vacuo to give 3-(2-pentyl-6-trifluoromethyl-pyridin-3-yl)-acrylic acid (340 mg, 97%).

Workup

  1. washwashed with EtOAc
  2. extractionThe solution was extracted three times with methylene chloride
  3. customdried over anhyd
  4. concentrationMgSO4 and concentrated in vacuo

Sources & evidence

ORD record
ord-b6281e49cff742859f3c59c3d8887d38
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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