Trimethyl phosphonoacetate → HCID 68295293, compound

HRID 1850059Notes

Reaction equation

HRID 1850059 reaction equation
[CH3:1][O:2][C:3]([CH2:5]P(OC)(OC)=O)=[O:4].C[O-].[Na+].[O:15]([CH2:22][CH2:23][N:24]1[CH:28]=[C:27]([CH:29]=O)[CH:26]=[N:25]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1>[O:15]([CH2:22][CH2:23][N:24]1[CH:28]=[C:27](/[CH:29]=[CH:5]/[C:3]([O:2][CH3:1])=[O:4])[CH:26]=[N:25]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 80029Trimethyl phosphonoacetateHCID 10942334Sodium MethoxideHCID 86702819HCID 86702819, compound

Product 1

HCID 68295293HCID 68295293, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Trimethyl phosphonoacetate (20.6 g, 112 mmol) was dissolved in 350 mL THF. A 25% w/w NaOMe solution (25 mL) was then added at room temperature and the resulting mixture was stirred for 30 min. 1-(2-Phenoxyethyl)-1H-pyrazole-4-carbaldehyde (24 g, 111 mmol) dissolved in 150 mL THF was added and the reaction mixture was stirred for 5 h before being quenched with aqueous ammonium chloride and extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated under vacuum. The residue was purified by column chromatography using a gradient of hexane/EtOAc (30:1 to 1:2) to yield (E)-methyl 3-(1-(2-phenoxyethyl)-1H-pyrazol-4-yl)acrylate (22 g, 72.7%).

Workup

  1. additionwas added
  2. stirringthe reaction mixture was stirred for 5 h
  3. custombefore being quenched with aqueous ammonium chloride
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-0d1cfd62720342e3890d88504bf7eafb
Source dataset
uspto-grants-2015_02
Patent number
US08957066B2

Reaction notes

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