Sodium Methoxide → (4-Methoxy-pyridin-2-yl)-methanol

HRID 2050774Notes

Reaction equation

HRID 2050774 reaction equation
C(O[C:5]1[C:6]([O:12][CH3:13])=[CH:7][C:8]([CH3:11])=[N:9][CH:10]=1)(=O)C.C[O-:15].[Na+]>CO>[OH:15][CH2:11][C:8]1[CH:7]=[C:6]([O:12][CH3:13])[CH:5]=[CH:10][N:9]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 19833705HCID 19833705, compound

Product 1

HCID 10820596(4-Methoxy-pyridin-2-yl)-methanolYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Starting with 2-methyl-4-methoxypyridine-1-oxide (2.1 g) in the procedure of Part (ii) afforded 2.5 g of 2-acetoxymethyl-4-methoxypyridine which was contaminated with about 25% of 5-acetoxy-2-methyl-4-methoxypyridine. This mixture was dissolved in methanol (10 ml) containing 1.118 g (20.7 mmole) sodium methoxide and stirred at reflux for one hour. The methanol was evaporated in vacuo, the residue diluted with water, neutralized with dilute hydrochloric acid and extracted with chloroform. The organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo to give 853 mg (41%) 2-hydroxymethyl-4-methoxypyridine. 1H-NMR(CDCl3)ppm (delta): 3.9 (s, 3H), 4.72 (s, 2H), 5.35 (bs, 1H), 6.7 (dd, 1H), 6.95 (d, 1H), 8.3 (d, 1H).

Workup

  1. temperatureat reflux for one hour
  2. customThe methanol was evaporated in vacuo
  3. additionthe residue diluted with water
  4. extractionextracted with chloroform
  5. washThe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-13a650b55c8446bea8d5a1ca35b167e0
Source dataset
uspto-grants-1991_05
Patent number
US05015473

Reaction notes

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