Water → HCID 67401333, compound

HRID 1186393Notes

Reaction equation

HRID 1186393 reaction equation
[H-].[Na+].[CH3:3][CH2:4][O:5][C:6]([CH:8](P(OCC)(OCC)=O)[CH3:9])=[O:7].[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]=O)[CH:19]=1.O>O1CCCC1.C(OCC)(=O)C>[CH3:9][C:8](=[CH:24][C:20]1[CH:19]=[N:18][CH:23]=[CH:22][CH:21]=1)[C:6]([O:5][CH2:4][CH3:3])=[O:7]

Participants

7

Reactant 4

HCID 962WaterHCID 103713-PyridinecarboxaldehydeHCID 24758Sodium hydrideHCID 107155Triethyl 2-phosphonopropionate

Product 1

HCID 67401333HCID 67401333, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sixty percent sodium hydride (in oil) (224 mg, 5.6 mmol) was suspended in tetrahydrofuran (5 mL). To this, triethyl 2-phosphonopropionate (1.2 mL, 5.6 mmol) was added under a nitrogen atmosphere with cooling in an ice bath and the mixture was stirred at the same temperature for 30 minutes. To this, 3-pyridinecarboxaldehyde (300 mg, 2.8 mmol) was added and the mixture was stirred at the same temperature for 1.5 hours. After water was added to the reaction mixture, extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous magnesium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0 to 2/1) to give ethyl 2-methyl-3-(pyridin-3-yl)acrylate (480 mg, yield: 90%).

Workup

  1. temperaturewith cooling in an ice bath
  2. stirringthe mixture was stirred at the same temperature for 1.5 hours
  3. washby washing with brine
  4. dry with materialdrying over anhydrous magnesium sulfate
  5. customThe solvent was evaporated off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0 to 2/1)

Sources & evidence

ORD record
ord-b954dccd708f4307ba82f9298d144e63
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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