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

HRID 2265957Notes

Reaction equation

HRID 2265957 reaction equation
C[O:2][C:3](=[O:21])[CH:4]=[CH:5][C:6]1[C:7]([N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[N:8][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:10][CH:11]=1.[Li+].[OH-]>C1COCC1.O>[CH2:19]([N:16]([CH2:17][CH3:18])[C:7]1[C:6]([CH:5]=[CH:4][C:3]([OH:21])=[O:2])=[CH:11][CH:10]=[C:9]([C:12]([F:15])([F:13])[F:14])[N:8]=1)[CH3:20]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 687797213-(2-Diethylamino-6-trifluoromethyl-pyridin-3-yl)-acrylic acid methyl ester

Product 1

HCID 687822843-(2-Diethylamino-6-trifluoromethyl-pyridin-3-yl)-acrylic acidYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 3-(2-diethylamino-6-trifluoromethyl-pyridin-3-yl)-acrylic acid methyl ester (40 mg, 0.132 mmol) in THF (1 ml) was added a solution of 0.5 N-LiOH (0.3 ml), and the mixture was stirred for 3 hours at room temperature. The resulting residue was dissolved in H2O and then washed three times with EtOAc, acidified with 1N HCl to pH 1˜2. The solution was extracted three times with methylene chloride and then dried over anhyd. Na2SO4 and concentrated in vacuo to give 3-(2-diethylamino-6-trifluoromethyl-pyridin-3-yl)-acrylic acid (33 mg, 87%).

Workup

  1. washwashed three times with EtOAc
  2. extractionThe solution was extracted three times with methylene chloride
  3. customdried over anhyd
  4. concentrationNa2SO4 and concentrated in vacuo

Sources & evidence

ORD record
ord-991170156bb9406fb1168582a6e75cdb
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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