Acetic Acid → Ethyl 3-(pyridin-2-yl)acrylate

HRID 478726Notes

Reaction equation

HRID 478726 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH:23]=O.C(O)(=O)C>C1COCC1.O>[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH:23]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 13345Triethyl phosphonoacetateHCID 142732-PyridinecarboxaldehydeHCID 24758Sodium hydride

Product 1

HCID 370265Ethyl 3-(pyridin-2-yl)acrylateYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (60% in oil, 0.88 g, 22 mmol) in THF (20 ml) was added ethyl diethylphosphonoacetate (4.93 g, 22 mmol) dropwise while ice cooling and the mixture was further stirred at room temperature for 15 minutes and again ice cooled. To the ice cooled mixture was added dropwise a solution of picolinaldehyde (2.14 g, 20 mmol) in THF (10 ml). After the addition, the reaction mixture was heated at 60° C. for 1 hour. Thereafter, the reaction was stopped by treating with 1M aqueous acetic acid. The mixture was diluted with water, and extracted with methylene chloride. The organic layer was treated according to conventional techniques. Evaporation of the solvent yielded a residue which was subjected to recrystallization from hexane to afford ethyl 3-(pyridin-2-yl)-acrylate, yield: 80%.

Workup

  1. temperatureagain ice cooled
  2. additionAfter the addition
  3. temperaturethe reaction mixture was heated at 60° C. for 1 hour
  4. extractionextracted with methylene chloride
  5. additionThe organic layer was treated
  6. customEvaporation of the solvent
  7. customyielded a residue which
  8. customwas subjected to recrystallization from hexane

Sources & evidence

ORD record
ord-039b2ba9be22495dab83edc015daf0b7
Source dataset
uspto-grants-2003_11
Patent number
US06642250B2

Reaction notes

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