Water → 2-Oxo-2-pyridin-3-ylethyl 2,2-dimethylpropanoate

HRID 478953Notes

Reaction equation

HRID 478953 reaction equation
[C:1]([OH:7])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C(=O)([O-])O.[Na+].Cl.Cl[CH2:15][C:16]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)=[O:17].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[CH3:3][C:2]([CH3:5])([CH3:4])[C:1]([O:7][CH2:15][C:16](=[O:17])[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)=[O:6]

Participants

7

Reactant 4

HCID 962WaterHCID 6417Pivalic acidHCID 516892Sodium BicarbonateHCID 116655522-Chloro-1-(pyridin-3-yl)ethan-1-one--hydrogen chloride (1/1)

Product 1

HCID 155124522-Oxo-2-pyridin-3-ylethyl 2,2-dimethylpropanoateYield 92.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Pivalic acid (5.3 g, 52 mmol), 8.8 g (104 mmol) of sodium hydrogen carbonate and 0.84 g (2.6 mmol) of tetrabutylammonium bromide were added to a solution of 5.0 g (26 mmol) of 3-(2-chloroacetyl) pyridine hydrochloride in 80 ml of THF at room temperature, and the mixture was refluxed for 2 hours. Water (100 ml) was added to the reaction mixture and the resulting mixture was extracted three times with 100 ml of ethyl acetate. The organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution and then dried over sodium sulfate. The solvent was distilled off under reduced pressure and the product was isolated and purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give 5.3 g (yield 92%) of the desired 2-oxo-2-pyridin-3-ylethyl 2,2-dimethylpropanoate.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. extractionthe resulting mixture was extracted three times with 100 ml of ethyl acetate
  3. washThe organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe product was isolated
  7. custompurified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-37d5b2a18ee44b9c83389172f40b86d8
Source dataset
uspto-grants-2003_11
Patent number
US06642387B2

Reaction notes

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