Dimethyl Sulfate → (3-Methoxy-6-methylpyridin-2-yl)methanol

HRID 1710885Notes

Reaction equation

HRID 1710885 reaction equation
[OH:1][CH2:2][C:3]1[C:8]([OH:9])=[CH:7][CH:6]=[C:5]([CH3:10])[N:4]=1.[CH3:11]OS(OC)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)=O>[CH3:11][O:9][C:8]1[C:3]([CH2:2][OH:1])=[N:4][C:5]([CH3:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 10796Cesium carbonateHCID 1351283-Hydroxy-2-hydroxymethyl-6-methylpyridine

Product 1

HCID 21882871(3-Methoxy-6-methylpyridin-2-yl)methanolYield 85%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-(hydroxymethyl)-6-methylpyridin-3-ol (1.23 g, 8.84 mmol) in acetone (25 mL) was added Me2SO4 (1 mL, 10.6 mmol), followed by Cs2CO3 (3.6 g, 11.05 mmol). The reaction was refluxed for 2 h. The reaction was filtered and concentrated to give a red oil which was purified by column chromatography on ISCO (40 g) with 0-80% ethyl acetate in hexanes over 25 minutes to yield (3-methoxy-6-methylpyridin-2-yl)methanol(1.15 g, 85% yield) as a off-white solid. HPLC retention time (Method B)=0.17 min. 1H NMR (CDCl3, 400 MHz) δ ppm 2.49 (s, 3H), 3.83 (s, 3H), 4.45 (s, 1H), 4.70 (s, 2H), 7.03 (s, 2H).

Workup

  1. temperatureThe reaction was refluxed for 2 h
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated
  4. customto give a red oil which
  5. customwas purified by column chromatography on ISCO (40 g) with 0-80% ethyl acetate in hexanes over 25 minutes

Sources & evidence

ORD record
ord-3be31b91a1d949048640622650011206
Source dataset
uspto-grants-2010_09
Patent number
US07790745B2

Reaction notes

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