Sodium Methoxide → HCID 68434912, compound

HRID 1867381Notes

Reaction equation

HRID 1867381 reaction equation
[CH3:1][O-:2].[Na+].[CH2:4]([O:11][C:12]1[C:13]([Cl:20])=[CH:14][C:15]([CH2:18]Cl)=[N:16][CH:17]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CO.CS(C)=O>[CH2:4]([O:11][C:12]1[C:13]([Cl:20])=[CH:14][C:15]([CH2:18][O:2][CH3:1])=[N:16][CH:17]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 455882855-(Benzyloxy)-4-chloro-2-(chloromethyl)pyridine

Product 1

HCID 68434912HCID 68434912, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 9.30 g (172 mmol) of sodium methylate in 132 ml methanol was added drop wise to a solution of 5-benzyloxy-4-chloro-2-chloromethyl-pyridine (Australian Journal of chemistry, 1977, 30, 649) in 130 ml DMSO. The suspension was heated at 100° C. for 6 h, poured on ice, extracted with four portions of CH3Cl. The organic phases were dried (Na2SO4), evaporated and distilled (Kp 0.2 mm Hg, 150-152° C.) to give 12.80 g (91%) of the title compound. MS: 264.0 (MH+).

Workup

  1. additionpoured on ice
  2. extractionextracted with four portions of CH3Cl
  3. dry with materialThe organic phases were dried (Na2SO4)
  4. customevaporated
  5. distillationdistilled (Kp 0.2 mm Hg, 150-152° C.)

Sources & evidence

ORD record
ord-b61a45a5b6444e0b8ee460498d5db197
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

Loading…