Dimethyl Sulfate → HCID 15158167, compound

HRID 466002Notes

Reaction equation

HRID 466002 reaction equation
[C:1]1([C:7]2[C:15]([C:16]#[C:17][C:18]([OH:20])=[O:19])=[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].S(OC)(O[CH3:27])(=O)=O>C(O)C>[C:1]1([C:7]2[C:15]([C:16]#[C:17][C:18]([O:20][CH3:27])=[O:19])=[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 15158166HCID 15158166, compound

Product 1

HCID 15158167HCID 15158167, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(2-Phenylpyrazolo[1,5-a]pyridin-3-yl)propiolic acid (10.33 g) was added to a mixture of sodium hydroxide (3.15 g) and 95% ethanol (103 g), and then dimethyl sulfate (4.97 g) was added to the mixture. The reaction mixture was heated at 60° to 80° C. for 3 hours and 20 minutes. Ethanol was evaporated in vacuo. Water was added to the residue and extracted with chloroform (50 ml×3). Combined extract was washed with a saturated aqueous solution of sodium chloride (50 ml), dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from ethyl acetate to give crystals of methyl 3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)propiolate (5.25 g).

Workup

  1. temperatureThe reaction mixture was heated at 60° to 80° C. for 3 hours and 20 minutes
  2. customEthanol was evaporated in vacuo
  3. additionWater was added to the residue
  4. extractionextracted with chloroform (50 ml×3)
  5. extractionCombined extract
  6. washwas washed with a saturated aqueous solution of sodium chloride (50 ml)
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ffb7bf1392ba4ced8800b13cc277f249
Source dataset
uspto-grants-1992_10
Patent number
US05155114

Reaction notes

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