4-Acetylpyridine → 2-(4-Pyridyl)-2-propanol

HRID 234645Notes

Reaction equation

HRID 234645 reaction equation
[CH3:1][Li].[C:3]([C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)(=[O:5])[CH3:4]>C(OCC)C.C1COCC1>[N:9]1[CH:10]=[CH:11][C:6]([C:3]([OH:5])([CH3:1])[CH3:4])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 142824-AcetylpyridineHCID 178418348HCID 178418348, compound

Product 1

HCID 45805832-(4-Pyridyl)-2-propanolYield 45%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyllithium (1.4 M; 30 ml, 42 mmol) in diethyl ether was added dropwise to a stirred solution of 4-acetylpyridine (4.65 ml, 42 mmol) in dry THF (100 ml) at -76° C., and the deep blue solution allowed to reach ambient temperature. After 24 hours the mixture was partitioned between ether and saturated aqueous sodium bicarbonate, and the ether phase was concentrated. Chromatography, on elution with ethyl acetate-dichloromethane-triethylamine 60:40:1, gave the title compound (2.59 g, 45%) as an oil. 1H-NMR (CDCl3) δ1.58 (6H, s, CMe2), 7.40 (2H, d, J 6.2 Hz, Py 3 and 5-H), 8.55 (2H, d, J 6.2 Hz, Py 2 and 6-H); MS m/z 137 (M+).

Workup

  1. customto reach ambient temperature
  2. customAfter 24 hours the mixture was partitioned between ether and saturated aqueous sodium bicarbonate
  3. concentrationthe ether phase was concentrated
  4. washChromatography, on elution with ethyl acetate-dichloromethane-triethylamine 60:40:1

Sources & evidence

ORD record
ord-87d4dced811c4384bd75d937942a0576
Source dataset
uspto-grants-1997_01
Patent number
US05595995

Reaction notes

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