Methanol → HCID 58478790, compound

HRID 1011352Notes

Reaction equation

HRID 1011352 reaction equation
[CH3:1][O:2][CH:3]=[CH:4][C:5]1[N:10]=[C:9]2[CH2:11][O:12][C:13](=[O:14])[C:8]2=[CH:7][CH:6]=1.[CH3:15][OH:16]>S(=O)(=O)(O)O>[CH3:1][O:2][CH:3]([O:16][CH3:15])[CH2:4][C:5]1[N:10]=[C:9]2[CH2:11][O:12][C:13](=[O:14])[C:8]2=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 67313859HCID 67313859, compound

Product 1

HCID 58478790HCID 58478790, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
70 °C

Procedure

To a solution of 2-(2-methoxy-vinyl)-7H-furo[3,4-b]pyridin-5-one (108 mg, 0.57 mmol) in anhydrous MeOH (10 mL) is added three drops of concentrated sulfuric acid. The reaction solution is stirred and heated at 70° C. for 18 h at which time the starting material is consumed. The reaction mixture is then diluted with EtOAc (100 mL), and then washed with saturated aqueous NaHCO3 (2×75 mL). The organic solution is dried (Na2SO4) and concentrated to give the title compound as a brown oil (104 mg, 83%).

Workup

  1. customis consumed
  2. additionThe reaction mixture is then diluted with EtOAc (100 mL)
  3. washwashed with saturated aqueous NaHCO3 (2×75 mL)
  4. dry with materialThe organic solution is dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-996aecdf31b64acf83eae33a05ba8ef6
Source dataset
uspto-grants-2011_07
Patent number
US07977351B2

Reaction notes

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