Water → HCID 66720746, compound

HRID 1639828Notes

Reaction equation

HRID 1639828 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH3:17][C:18]1[N:28]=[C:21]2[CH:22]=[CH:23][CH:24]=[C:25]([CH:26]=O)[N:20]2[N:19]=1.O>O1CCCC1>[CH3:17][C:18]1[N:28]=[C:21]2[CH:22]=[CH:23][CH:24]=[C:25](/[CH:26]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:20]2[N:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 59334616HCID 59334616, compound

Product 1

HCID 66720746HCID 66720746, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of sodium hydride (0.570 g, 13.0 mmol) in tetrahydrofuran (50 mL) was added a solution of ethyl diethylphosphonoacetate (2.36 mL, 11.8 mmol) in tetrahydrofuran (10 mL) at 0° C., and the mixture was stirred for 20 min. To the reaction mixture was added a solution of 2-methyl[1,2,4]triazolo[1,5-a]pyridine-5-carbaldehyde (1.90 g, 11.8 mmol) in tetrahydrofuran (58 mL), and the mixture was warmed to room temperature over 4 hr. Water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/2) to give the title compound (2.50 g, yield 92%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/2)

Sources & evidence

ORD record
ord-88b2dcfaa503461c8f4dbee463ca5efe
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

Loading…