(2-Chloropyridin-4-yl)methanol → (2-Methoxypyridin-4-yl)methanol

HRID 426242Notes

Reaction equation

HRID 426242 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1.[CH3:10][O-:11].[Na+]>>[CH3:10][O:11][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 7062237(2-Chloropyridin-4-yl)methanolHCID 10942334Sodium Methoxide

Product 1

HCID 14462410(2-Methoxypyridin-4-yl)methanolYield 60%

Procedure

(2-Chloro-pyridin-4-yl)-methanol (2.82 g, 19.67 mmol) was refluxed with 25 wt. % sodium methoxide (25 ml) solution for 24 hr. After cooling to room temperature, the mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA:hexane (1:1)) to afford 1.8 g (60%) of (2-Methoxy-pyridin-4-yl)-methanol as a pale brown oil. 1H NMR (200 MHz, CDCl3) δ 2.16 (3H, s), 2.21 (3H, s), 5.13 (2H, s), 6.99 (1H, d, J=5.6 Hz), 8.11 (1H, br. s), 8.12 (1H, s), 8.23 (1H, d, J=5.6 Hz).

Workup

  1. customthe mixture was evaporated in vacuo
  2. customthe residue was purified by silica gel column chromatography (eluent, EA:hexane (1:1))

Sources & evidence

ORD record
ord-28a7b9531af14b60be96ec1182cb0212
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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