Water → HCID 22270370, compound

HRID 2104278Notes

Reaction equation

HRID 2104278 reaction equation
[C:1]([O-:6])(=[O:5])[CH:2]([CH3:4])[OH:3].[Li+].[H-].[Na+].Cl[C:11]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][N:12]=1.O>CN(C)C=O>[F:18][C:17]([F:20])([F:19])[C:15]1[CH:14]=[CH:13][N:12]=[C:11]([O:3][CH:2]([CH3:4])[C:1]([OH:6])=[O:5])[CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1449582-Chloro-4-(trifluoromethyl)pyridineHCID 23673452Propanoic acid, 2-hydroxy-, lithium salt (1:1)

Product 1

HCID 22270370HCID 22270370, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of lithium lactate (7.8 g, 81 mmol) in 100 mL of anhydrous dimethylformamide was added sodium hydride (60% dispersion in mineral oil, 3.2 g, 80 mmol). After stirring at room temperature for 30 min, 2-chloro-4-trifluromethylpyridine (10 g, 55 mmol) was added, and the mixture was heated at 100° C. overnight. The reaction was cooled to room temperature, poured into 500 mL of water, and was washed with hexane (200 mL). The aqueous solution was acidified with concentrated hydrochloric acid (pH>2), and was extracted with ether (2×500 mL). The combined extracts were washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated to dryness to give the title compound.

Workup

  1. temperaturethe mixture was heated at 100° C. overnight
  2. temperatureThe reaction was cooled to room temperature
  3. washwas washed with hexane (200 mL)
  4. extractionwas extracted with ether (2×500 mL)
  5. washThe combined extracts were washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-db261376cbb64f48a70501729070d0ad
Source dataset
uspto-grants-2009_08
Patent number
US07576239B2

Reaction notes

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