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

HRID 1761401Notes

Reaction equation

HRID 1761401 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-dec2e2f8006147c882c6328cd4dcebde
Source dataset
uspto-grants-1989_05
Patent number
US04826833

Reaction notes

Loading…