Ethanol → Ethyl 2-(2-methylpyridin-3-yl)acetate

HRID 889297

Reaction equation

HRID 889297 reaction equation
[CH3:1][C:2]1[C:7]([CH2:8][C:9]#N)=[CH:6][CH:5]=[CH:4][N:3]=1.S(=O)(=O)(O)O.C(=O)(O)[O-:17].[Na+].[CH2:21]([OH:23])[CH3:22]>>[CH2:21]([O:23][C:9](=[O:17])[CH2:8][C:7]1[C:2]([CH3:1])=[N:3][CH:4]=[CH:5][CH:6]=1)[CH3:22]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium Bicarbonate2×HCID 190992862-(2-Methylpyridin-3-yl)acetonitrile

Product 1

HCID 15169545Ethyl 2-(2-methylpyridin-3-yl)acetate

Procedure

790 mg (5.98 mmol) of the compound from Example 38A are initially introduced into 10 ml ethanol, 4 ml concentrated sulfuric acid are added slowly and the mixture is heated under reflux for 6 h. After cooling, the mixture is neutralized with 6.00 g sodium bicarbonate and saturated sodium bicarbonate solution. The aqueous phase is extracted several times with ethyl acetate and the combined organic phases are dried over sodium sulfate, filtered and concentrated. The residue is reacted without further purification.

Workup

  1. additionare added slowly
  2. temperaturethe mixture is heated
  3. temperatureunder reflux for 6 h
  4. temperatureAfter cooling
  5. extractionThe aqueous phase is extracted several times with ethyl acetate
  6. dry with materialthe combined organic phases are dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is reacted without further purification

Sources & evidence

ORD record
ord-dac4c7b3d4e940e9ad4727c046d316a8
Source dataset
uspto-grants-2012_08
Patent number
US08252817B2

Linked notes

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