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

HRID 1526077

Reaction equation

HRID 1526077 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-26c686c181134a499eb02e8399b224bf
Source dataset
uspto-grants-2015_07
Patent number
US09085572B2

Linked notes

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