3-Acetylpyridine → 2-(Pyridin-3-yl)propan-2-ol

HRID 234649Notes

Reaction equation

HRID 234649 reaction equation
[CH3:1][Li].[C:3]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)(=[O:5])[CH3:4]>C(OCC)C.C1COCC1>[N:8]1[CH:9]=[CH:10][CH:11]=[C:6]([C:3]([OH:5])([CH3:1])[CH3:4])[CH:7]=1

Participants

5

Reactant 2

HCID 95893-AcetylpyridineHCID 178418348HCID 178418348, compound

Product 1

HCID 107254032-(Pyridin-3-yl)propan-2-olYield 46%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

The method followed that of Example 4a, but using methyllithium (1.4 M; 14 ml, 20 mmol) in diethyl ether and 3-acetylpyridine (2.2 ml, 20 mmol) in dry THF (40 ml). Work-up and chromatography, on elution with ether-petrol-triethylamine 30:10:1, afforded the title compound (1.26 g, 46%) as an oil. 1H-NMR (CDCl3) δ1.58 (6H, s, CMe2), 7.22 (1H, m, Py 5-H), 7.85 (1H, m, Py 4-H), 8.32 (1H, m, Py 6-H), 8.65 (1H, m, Py 2-H); MS m/z 137 (M+).

Workup

  1. washchromatography, on elution with ether-petrol-triethylamine 30:10:1

Sources & evidence

ORD record
ord-e3c59f38d99a4c32957f2983dacff228
Source dataset
uspto-grants-1997_01
Patent number
US05595995

Reaction notes

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