Water → {[4-(Trifluoromethyl)pyridin-2-yl]methoxy}acetic Acid

HRID 2367052Notes

Reaction equation

HRID 2367052 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][OH:10])[CH:4]=1.[H-].[Na+].Br[CH2:16][C:17]([O:19]C(C)(C)C)=[O:18].O>CN(C=O)C>[F:12][C:2]([F:11])([F:1])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][O:10][CH2:16][C:17]([OH:19])=[O:18])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 147614592-(Hydroxymethyl)-4-(trifluoromethyl)pyridine

Product 1

HCID 57803266{[4-(Trifluoromethyl)pyridin-2-yl]methoxy}acetic Acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of [4-(trifluoromethyl)pyridin-2-yl]methanol (340 mg, 1.9 mmol) in DMF (10 mL) was added sodium hydride (150 mg, 3.8 mmol). After being stirred at room temperature for 5 min. 1,1-dimethylethyl bromoacetate (0.28 mL, 1.9 mmol) was added. Stirring was continued at room temperature for 1 h. Water (20 mL) was added and the resulting solution was extracted with EtOAc. The water layer was neutralized to pH=5 with HCl and extracted with EtOAc twice. The combined organic layers were dried (MgSO4) and concentrated under vacuum to give the title compound which was used for the next reaction without purification. MS (M+H) 292.2.

Workup

  1. stirringStirring
  2. waitwas continued at room temperature for 1 h
  3. extractionthe resulting solution was extracted with EtOAc
  4. extractionextracted with EtOAc twice
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3f78b1e6b3da430093d9843f79d1905a
Source dataset
uspto-grants-2014_04
Patent number
US08697870B2

Reaction notes

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