Water → HCID 68458630, compound

HRID 499606Notes

Reaction equation

HRID 499606 reaction equation
[H-].[Na+].C(OP([CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH:24]=O.O>O1CCCC1>[CH3:17][C:11](=[CH:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 142732-PyridinecarboxaldehydeHCID 24758Sodium hydrideHCID 107155Triethyl 2-phosphonopropionate

Product 1

HCID 68458630HCID 68458630, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Sodium hydride (ca. 60%, 2.0 g, 50.0 mmol) was suspended in tetrahydrofuran (20 ml), and a solution of ethyl 2-(diethylphosphono)propionate (11.7 g, 49.1 mmol) in tetrahydrofuran (8 ml) was added thereto under ice cooling condition. The mixture was stirred for 0.5 hr. Successively, a solution of 2-pyridinecarbaldehyde (5.0 g, 46.7 mmol) in tetrahydrofuran (8 ml) was added to the mixture. The mixture was stirred at 0° C. for 14 hrs, combined with water, concentrated under reduced pressure to the half amount and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was subjected to a silica gel (80 g) column chromatography. The fractions eluted with hexane-ethyl acetate (3:1, v/v) were collected and concentrated to give the titled compound (7.8 g, 87%).

Workup

  1. stirringThe mixture was stirred at 0° C. for 14 hrs
  2. concentrationconcentrated under reduced pressure to the half amount
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. washThe fractions eluted with hexane-ethyl acetate (3:1
  8. customv/v) were collected
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d9861692f80d4bd3a3f7171c007d8b59
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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