Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 6-(2-hydroxyethyl)-6H-furo[2,3-c]pyridin-7-one

HRID 2196062Notes

Reaction equation

HRID 2196062 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O1CCCCC1[O:24][CH2:25][CH2:26][N:27]1[CH:32]=[CH:31][C:30]2[CH:33]=[CH:34][O:35][C:29]=2[C:28]1=[O:36].C(=O)([O-])O.[Na+]>CO>[OH:24][CH2:25][CH2:26][N:27]1[CH:32]=[CH:31][C:30]2[CH:33]=[CH:34][O:35][C:29]=2[C:28]1=[O:36]

Participants

5

Reactant 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 686754816-[2-(tetrahydropyran-2-yloxy)ethyl]-6H-furo[2,3-c]pyridin-7-one

Product 1

HCID 686744936-(2-hydroxyethyl)-6H-furo[2,3-c]pyridin-7-oneYield 73.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Pyridinium p-toluenesulfonate (0.21 g, 0.85 mmol) was added to a methanol solution (20 ml) of 6-[2-(tetrahydropyran-2-yloxy)ethyl]-6H-furo[2,3-c]pyridin-7-one (0.45 g, 1.7 mmol), and stirred at room temperature for 2 days. An aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Diethyl ether was added to the residue to precipitate crystals. The crystals were collected by filtration and dried to thereby obtain 223 mg (yield: 73%) of 6-(2-hydroxyethyl)-6H-furo[2,3-c]pyridin-7-one as a white powder.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. additionDiethyl ether was added to the residue
  5. customto precipitate crystals
  6. filtrationThe crystals were collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-3de3215239604ee49de91cff1418ad12
Source dataset
uspto-grants-2012_12
Patent number
US08338406B2

Reaction notes

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