(6-Methylpyridin-3-yl)methanol
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(6-Methylpyridin-3-yl)methanol
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CAS No:
34107-46-5
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Formula:
C7H9NO
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Chemical Name:
(6-Methylpyridin-3-yl)methanol
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Synonyms:
5-(Hydroxymethyl)-2-methylpyridine;(6-methyl-3-pyridinyl)methanol;6-Methylpyridine-3-methanol;(6-Methylpyridin-3-yl)methanol, 5-(Hydroxymethyl)-2-picoline;6-Methyl-3-PyridineMethanol;5-Hydroxymethyl-2-methylpyridine 97%;3-Pyridinemethanol, 6-methyl-
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CAS No:
Safety Information
IRRITANT
NONH for all modes of transport
3
22-37/38-41
26-39
Xi,Xn
P261-P280-P305 + P351 + P338
H302-H315-H318-H335
(6-Methylpyridin-3-yl)methanol Use and Manufacturing
To a stirred solution of compound 11(21 g; 140 mmol; 1 eq) in dry THF (150 mL) was added 1M LiA1H4 solution in THF (210 mL; 210 mmol; 1.5 eq) dropwise at -5 °C and after completion of the addition it was stirred at 23 °C for 2 h. The mixture was cooled to -10°C and quenched with sodium sulfate decahydrate and ethyl acetate until effervescence ceased. The mixture was filtered through a Celite® pad and the filtrate was evaporated to dryness to afford the title compound (17 g, 100percent). 1H NMR (DMSO-d6) ö 8.37 (s, 1H), 7.59 (dd, 1H, J = 2, 8 Hz), 7.19 (d, 1H, J = 8 Hz), 5.22 (t, 1H, J = 6 Hz), 4.47 (d, 2H, J = 6 Hz), 2.45 (s, 3H).To a solution of LiAlH4 (80.0 g, 2.11 mol) in anhydrous THF (1 L) at 0C, a solution ofmethyl 6-methylnicotinate (1, 200 g, 1.32 mol) in THF (1 L) was added dropwise. Afterstirring at 0C for 3 h, the reaction mixture was quenched with saturated aqueous Na2SO4(ca. 150 mL, 0.43 mol) at 0C. The mixture was filtered, and the solid washed with ethylacetate. The organic layer of filtrate was separated and dried over anhydous MgSO4. Solventwas removed to give 2 as a yellow oil (160 g, 98percent). Its 1H NMR data data matchedthose previously reported.27, 28 HPLC > 99percent.
5-Hydroxymethyl-2-methylpyridine is a reactant used in the preparation of pioglitazone (P471000) metabolites.
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