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

HRID 1802747Notes

Reaction equation

HRID 1802747 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH2:15][CH3:16])=[N:8][N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=12)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH2:15]([C:7]1[C:6]([CH2:4][OH:3])=[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][N:9]2[N:8]=1)[CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 137381512-Ethyl-pyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 57899265(2-Ethyl-pyrazolo[1,5-a]pyridin-3-yl)methanolYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-ethyl-pyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester (15 g, 68.7 mmol) in tetrahydrofuran (300 mL) was cooled in an ice bath and lithium aluminum hydride (2.6 g, 68.7 mmol) was added. The reaction mixture was stirred at room temperature for 16 h. Water was added until bubbling stopped. Silica gel was added and the solvent was evaporated in vacuo. The resulting residue was purified via silica chromatography (20-100% ethyl acetate/heptane) to yield the title compound as a yellow/brown oil (9.67 g, 80% yield).

Workup

  1. customuntil bubbling
  2. additionSilica gel was added
  3. customthe solvent was evaporated in vacuo
  4. customThe resulting residue was purified via silica chromatography (20-100% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-3c5cefecdcfe465da5b1fdfa1119cba0
Source dataset
uspto-grants-2013_01
Patent number
US08349883B2

Reaction notes

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