Water → (2-Methylpyridin-4-yl)methanol

HRID 1384626Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([C:8](OC)=[O:9])[CH:5]=[CH:4][N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>CCOCC>[OH:9][CH2:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=1

Participants

Conditions

Temperature: 5 °C

Procedure

A solution of methyl 2-methyl-pyridine-4-carboxylate (800 mg, 6 mmol) in ether (5 ml) was added to lithium aluminium hydride (340 mg, 9 mmol) in ether (10 ml) cooled to 5° C. and the mixture stirred for 2 hours. Water was added, the mixture was filtered through diatomaceous earth and the pad was washed through with ethyl acetate. The filtrate was extracted with ethyl acetate and the combined extracts were washed with brine, dried (MgSO4) and the solvent removed by evaporation to give 4-hydroxymethyl-2-methylpyridine (240 mg, 38%) as a yellow oil. 1H NMR Spectrum: (CDCl3)2.48(s, 3H); 5.44(s, 2H); 7.00(d, 1H); 7.10(s, 1H); 8.40(d, 1H) MS-ESI: 124 [MH]+

Workup

filtrationthe mixture was filtered through diatomaceous earth
washthe pad was washed through with ethyl acetate
extractionThe filtrate was extracted with ethyl acetate
washthe combined extracts were washed with brine
dry with materialdried (MgSO4)
customthe solvent removed by evaporation

Sources & evidence

ORD record: ord-c24e05d447bb4318a03b1be80787f291
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06258951B1

Reaction notes

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