(2-Ethyl-pyrazolo[1,5-a]pyridin-3-yl)methanol → 2-Ethyl-pyrazolo[1,5-a]pyridine-3-carbaldehyde

HRID 549375Notes

Reaction equation

HRID 549375 reaction equation
[CH2:1]([C:3]1[C:11]([CH2:12][OH:13])=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2]>O1CCCC1.O=[Mn]=O>[CH2:1]([C:3]1[C:11]([CH:12]=[O:13])=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 57899265(2-Ethyl-pyrazolo[1,5-a]pyridin-3-yl)methanol

Product 1

HCID 234693952-Ethyl-pyrazolo[1,5-a]pyridine-3-carbaldehydeYield 98.3%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-ethyl-pyrazolo[1,5-a]pyridin-3-yl)-methanol (9.67 g, 54.9 mmol) in tetrahydrofuran (500 mL) was added MnO2 (23.88 g, 274.5 mmol, 85%, dried in oven at 120° C. for 16 h) and stirred at the reflux temperature for 1.5 h. The reaction mixture was filtered through a Celite pad, and concentrated under reduced pressure to give 9.4 g (98%) of product, which was used without further purification.

Workup

  1. filtrationThe reaction mixture was filtered through a Celite pad
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b2f53e6e739644168ce9f7fb48a012be
Source dataset
uspto-grants-2011_05
Patent number
US07943652B2

Reaction notes

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