6-Ethoxycarbonyl-4,5,6,7-tetrahydrofuro[2,3-c]pyridin-4-one → 6-Methyl-4,5,6,7-tetrahydrofuro[2,3-c]pyridin-4-ol
Reaction equation
C(O[C:4]([N:6]1[CH2:11][C:10](=[O:12])[C:9]2[CH:13]=[CH:14][O:15][C:8]=2[CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:4][N:6]1[CH2:11][CH:10]([OH:12])[C:9]2[CH:13]=[CH:14][O:15][C:8]=2[CH2:7]1Participants
Procedure
A solution of 1.76 g of 6-ethoxycarbonyl-4,5,6,7-tetrahydrofuro[2,3-c]pyridin-4-one prepared in the step 4 in 20 mL of dry THF was slowly dropped into an ice-cooled solution of 0.45 g of lithium aluminum hydride in 20 mL of dry THF. The reaction solution was gradually heated followed by heating to reflux for 30 minutes. The reaction solution was cooled, an excess of lithium aluminum hydride was decomposed by a gradual addition of ice thereto and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated solution of sodium chloride and dried over anhydrous magnesium sulfate and the solvent was evaporated therefrom in vacuo. The residue was purified by silica gel column chromatography to give 1.03 g of the objective compound.
Workup
- temperatureThe reaction solution was gradually heated
- temperatureby heating
- temperatureto reflux for 30 minutes
- temperatureThe reaction solution was cooled
- extractionthe mixture was subjected to extraction with ethyl acetate
- washThe organic layer was washed with a saturated solution of sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-9ac84e18e391499fb4b4aced17e184c9
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08217031B2
Reaction notes
Loading…