Sodium → 5-(Benzyloxy)-2-(methoxymethyl)pyridine

HRID 2273531Notes

Reaction equation

HRID 2273531 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15]Cl)=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][O-:18].[Na+].[Na]>CO.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][O:18][CH3:17])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 178541585-(Benzyloxy)-2-(chloromethyl)pyridine

Product 1

HCID 575003505-(Benzyloxy)-2-(methoxymethyl)pyridineYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

50 g (0.21 mol) of 5-benzyloxy-2-chloromethylpyridine (CAS 127590-90-3; D. I. Scopes, N. F. Norman, D. E. Bays, D. Belton, J. Brain et al., J. Med. Chem., 1992, 35, 490-501) in solution in 150 ml of methanol are added to the solution of sodium methoxide prepared by adding 6.4 g (0.28 mol) of sodium to 150 ml of methanol. After refluxing for 3 hours under nitrogen, the solution is concentrated to dryness. The oil obtained is taken up in ethyl acetate. The solution is washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulphate and then concentrated to dryness. 46 g (94%) of a brown oil are obtained.

Workup

  1. customprepared
  2. temperatureAfter refluxing for 3 hours under nitrogen
  3. concentrationthe solution is concentrated to dryness
  4. customThe oil obtained
  5. washThe solution is washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-b8b85eca74ed441eb2fe664f4b940ceb
Source dataset
uspto-grants-2015_09
Patent number
US09120819B2

Reaction notes

Loading…