Sodium Methoxide → 7-Methoxyfuro[2,3-C]pyridine

HRID 564711Notes

Reaction equation

HRID 564711 reaction equation
Cl[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9][O:8][C:7]=12.[CH3:11][O-:12].[Na+]>O1CCOCC1.O>[CH3:11][O:12][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9][O:8][C:7]=12

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 128261077-Chlorofuro[2,3-c]pyridine

Product 1

HCID 105829307-Methoxyfuro[2,3-C]pyridineYield 89.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 7-chlorofuro[2,3-c]pyridine (1.1 g) was stirred at room temperature under dry nitrogen in 1,4-dioxane (40 ml). Sodium methoxide (1.2 g) was added and the resulting mixture heated at reflux overnight. The mixture was diluted with water (100 ml) then extracted with ethyl acetate (3×100 ml). The combined organic extracts were washed with brine (50 ml), dried over magnesium sulfate, filtered and the solvent removed in vacuo to give the title compound (0.96 g) as a brown oil.

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux overnight
  3. extractionthen extracted with ethyl acetate (3×100 ml)
  4. washThe combined organic extracts were washed with brine (50 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-2f82e15f3d06450296a6e39f023fca70
Source dataset
uspto-grants-2001_01
Patent number
US06169090A

Reaction notes

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