Lithium Hydroxide → 3-(2-Phenethyl-6-trifluoromethyl-pyridin-3-yl)-acrylic acid

HRID 2266015Notes

Reaction equation

HRID 2266015 reaction equation
[CH2:1]([C:9]1[C:14]([CH:15]=[CH:16][C:17]([O:19]C)=[O:18])=[CH:13][CH:12]=[C:11]([C:21]([F:24])([F:23])[F:22])[N:10]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Li+].[OH-]>C1COCC1.O>[CH2:1]([C:9]1[C:14]([CH:15]=[CH:16][C:17]([OH:19])=[O:18])=[CH:13][CH:12]=[C:11]([C:21]([F:23])([F:22])[F:24])[N:10]=1)[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 72335657HCID 72335657, compound

Product 1

HCID 687795243-(2-Phenethyl-6-trifluoromethyl-pyridin-3-yl)-acrylic acidYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of compound 3-(2-phenethyl-6-trifluoromethyl-pyridin-3-yl)-acrylic acid, methyl ester (1.46 g, 4.35 mmol) in THF (3 ml) was added a solution of 1 N-LiOH (6.0 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-phenethyl-6-trifluoromethyl-pyridin-3-yl)-acrylic acid (1.37 g, 98%).

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-c09479b98b9e4ed2804631670ae8fc06
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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