Water → HCID 59750189, compound

HRID 748332Notes

Reaction equation

HRID 748332 reaction equation
[CH2:1]([P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])P(=O)(OCC)OCC.[H-].[Na+].[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:26]=O.O>O1CCCC1>[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1/[CH:26]=[CH:1]/[P:10](=[O:17])([O:11][CH2:12][CH3:13])[O:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 142732-PyridinecarboxaldehydeHCID 15455Tetraethyl methylenediphosphonateHCID 24758Sodium hydride

Product 1

HCID 59750189HCID 59750189, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of tetraethyl methylenediphosphonate (3.7 g, 13 mmol) in tetrahydrofuran (5 ml) was added dropwise to a mixture of sodium hydride (60% in oil, 750 mg, 18 mmol) and tetrahydrofuran (15 ml) at 0° C., and the mixture was stirred at the same temperature for 20 minutes. Successively, a solution of 2-pyridinecarbaldehyde (1.3 g, 12 mmol) in tetrahydrofuran (5 ml) was added dropwise to the mixture at 0° C., and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was combined with water and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with ethyl acetate-methanol (20:1, v/v) were collected and concentrated to give the titled compound (2.7 g, 94%).

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. washThe fractions eluted with ethyl acetate-methanol (20:1
  7. customv/v) were collected
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-02793c34fe9e4d6d90424b5b5fcc0552
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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