3-[4-(1h-Pyrazol-1-yl)phenyl]-2-propyn-1-ol → 3-[4-(1H-pyrazol-1-yl)phenyl]-2-propynal

HRID 1166094Notes

Reaction equation

HRID 1166094 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]#[C:13][CH2:14][OH:15])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1>CC(C)=O.O=[Mn]=O>[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]#[C:13][CH:14]=[O:15])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

4

Reactant 1

HCID 226309253-[4-(1h-Pyrazol-1-yl)phenyl]-2-propyn-1-ol

Product 1

HCID 226308103-[4-(1H-pyrazol-1-yl)phenyl]-2-propynalYield 27%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 180AcetoneSolvent

Procedure

A mixture of the compound from step A (0.71 g, 3.58 mmol) and MnO2 (3.10 g, 35.66 mmol) in acetone (40 mL) was heated to reflux for 3 h. The cooled reaction mixture was filtered through Celite and the filtrate was concentrated. Purification by chromatography (SiO2, 6:1 hexane/ethyl acetate) yielded 0.19 g (27%) of the title compound as an off-white solid. MS 197 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. customThe cooled reaction mixture
  4. filtrationwas filtered through Celite
  5. concentrationthe filtrate was concentrated
  6. customPurification by chromatography (SiO2, 6:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-cbd51eabece04896a9399fa808ca7823
Source dataset
uspto-grants-2003_09
Patent number
US06613747B2

Reaction notes

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