Sodium → HCID 57500339, compound

HRID 2273524Notes

Reaction equation

HRID 2273524 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH2:15]Cl)=[N:11][CH:12]=[CH: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.O>[CH2:1]([O:8][C:9]1[C:10]([CH2:15][O:18][CH3:17])=[N:11][CH:12]=[CH: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 57500338HCID 57500338, compound

Product 1

HCID 57500339HCID 57500339, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

The solution of 41 g (0.18 mol) of 3-(benzyloxy)-2-(chloromethyl)pyridine in 100 ml of methanol is added to the solution of sodium methoxide, prepared by adding 5.2 g (0.23 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 water and extracted with ethyl acetate. The organic solution is washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulphate, and then concentrated to dryness. 39 g (97%) 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. extractionextracted with ethyl acetate
  6. washThe organic solution is washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulphate
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-5a2461b5142b452ab2d906f117e79e37
Source dataset
uspto-grants-2015_09
Patent number
US09120819B2

Reaction notes

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