Ethyl Acetate → HCID 5371891, compound

HRID 398396Notes

Reaction equation

HRID 398396 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]=O.[CH3:11][CH2:12][O:13][C:14]([CH3:16])=[O:15]>C1COCC1.O>[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[CH:9]=[CH:16]/[C:14]([O:13][CH2:12][CH3:11])=[O:15]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 142732-PyridinecarboxaldehydeHCID 24758Sodium hydride

Product 1

HCID 5371891HCID 5371891, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of triethyl phosphonoacetate (10.5 g, 47 mmol) in THF (100 mL) at 0° C. was added sodium hydride (2.2 g of a 60% suspension in mineral oil, 55 mmol) in portions over a period of 30 min, followed by pyridine 2-carboxaldehyde (5.0 g, 47 mmol). The resulting solution was stirred at 0° C. for 1 h and then at ambient temperature for 18 h. The solution was diluted with EtOAc and water. The organic phase was separated, washed with water, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography using a gradient elution of 15-25% EtOAc:hexanes to give the title compound as a colorless liquid (6.0 g; TLC Rf=0.5, 1:2 EtOAc:hexanes).

Workup

  1. waitat ambient temperature for 18 h
  2. customThe organic phase was separated
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography
  8. washa gradient elution of 15-25% EtOAc

Sources & evidence

ORD record
ord-409aa239aed94a3f83af5fe2483cd99c
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Reaction notes

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