Water → HCID 59750108, compound

HRID 499615Notes

Reaction equation

HRID 499615 reaction equation
C(OP([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[CH3:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][N:27]=1)[CH:23]=O.O>O1CCCC1>[CH3:19][C:20]1[CH:21]=[C:22](/[CH:23]=[CH:9]/[C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH:25]=[CH:26][N:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27630002-METHYLISONICOTINALDEHYDEHCID 2773685tert-Butyl diethylphosphonoacetate

Product 1

HCID 59750108HCID 59750108, compoundYield 48.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of tert-butyl diethylphosphonoacetate (12.4 g, 49 mmol) in tetrahydrofuran (30 ml) was added dropwise to a mixture of sodium hydride (60% in oil, 2.3 g, 57 mmol) and tetrahydrofuran (100 ml) at 0° C., and the mixture was stirred at the same temperature for 30 minutes. Successively, a solution of 2-methylisonicotinaldehyde (5.0 g, 41 mmol) in tetrahydrofuran (20 ml) was added to the mixture at 0° C., and the mixture was stirred at room temperature for 1 hr. The reaction mixture was combined with water 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 column chromatography. The fractions eluted with ethyl acetate-hexane (2:3, v/v) were collected and concentrated to give the titled compound (4.4 g, 48%).

Workup

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

Sources & evidence

ORD record
ord-79c46d2592924b48be7669dda3def1ea
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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