Sulfuric Acid → Prop-2-yn-1-yl [3-methyl-1-(4-methylpyridin-3-yl)-5-phenyl-1H-pyrazol-4-yl]acetate

HRID 888727Notes

Reaction equation

HRID 888727 reaction equation
[CH2:1](O)[C:2]#[CH:3].S(=O)(=O)(O)O.[CH3:10][C:11]1[C:15]([CH2:16][C:17]([OH:19])=[O:18])=[C:14]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:13]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][C:31]=2[CH3:32])[N:12]=1>>[CH3:10][C:11]1[C:15]([CH2:16][C:17]([O:19][CH2:3][C:2]#[CH:1])=[O:18])=[C:14]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:13]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][C:31]=2[CH3:32])[N:12]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7859Propargyl alcoholHCID 68818330[3-Methyl-1-(4-methylpyridin-3-yl)-5-phenyl-1H-pyrazol-4-yl]acetic acid

Product 1

HCID 86626935Prop-2-yn-1-yl [3-methyl-1-(4-methylpyridin-3-yl)-5-phenyl-1H-pyrazol-4-yl]acetate

Procedure

0.445 g (6.345 mmol) of prop-2-yn-1-ol and a drop of concentrated sulfuric acid were added to 0.130 g (0.423 mmol) of [3-methyl-1-(4-methylpyridin-3-yl)-5-phenyl-1H-pyrazol-4-yl]acetic acid, and the mixture was stirred under reflux for 4 h. The solvent was removed under reduced pressure, a mixture of 10 ml of dichloromethane, 1.5 ml of diisopropylethylamine and 10 ml of water was added to the residue and the aqueous phase was extracted with 15 ml of dichloromethane. The combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. Chromatography of the residue gave 0.083 g (57% of theory) of a light-beige solid of melting point 106° C.

Workup

  1. temperatureunder reflux for 4 h
  2. customThe solvent was removed under reduced pressure
  3. additiona mixture of 10 ml of dichloromethane, 1.5 ml of diisopropylethylamine and 10 ml of water
  4. additionwas added to the residue
  5. extractionthe aqueous phase was extracted with 15 ml of dichloromethane
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customChromatography of the residue gave 0.083 g (57% of theory) of a light-beige solid of melting point 106° C.

Sources & evidence

ORD record
ord-5153b4bb6c5a46b5985d43a4d03cc774
Source dataset
uspto-grants-2012_08
Patent number
US08252723B2

Reaction notes

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