Sodium 5-oxo-2,5-dihydrofuran-3-carboxylate → 2-Oxooxolane-4-carboxylic acid
Reaction equation
[O:1]=[C:2]1[O:6][CH2:5][C:4]([C:7]([O-:9])=[O:8])=[CH:3]1.[Na+].[H][H]>O.[Pd]>[O:1]=[C:2]1[O:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of sodium 5-oxo-2,5-dihydrofuran-3-carboxylate (150 mg) in water (3 ml) was added 10 wt % palladium on carbon (30 mg), and the mixture was stirred for 18 hours at room temperature under one atm. of hydrogen. Under nitrogen atmosphere, an appropriate amount of amberlite IR-120 was added to the reaction solution, the mixture was stirred at room temperature for 10 minutes, and then filtered through Celite. The filtrate was concentrated under reduced pressure, ethyl acetate was added to the resulting residue, the mixture was dried over sodium sulfate, and then again concentrated under reduced pressure to give the titled compound (83 mg).
Workup
- additionUnder nitrogen atmosphere, an appropriate amount of amberlite IR-120 was added to the reaction solution
- filtrationfiltered through Celite
- concentrationThe filtrate was concentrated under reduced pressure, ethyl acetate
- additionwas added to the resulting residue
- dry with materialthe mixture was dried over sodium sulfate
- concentrationagain concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-21e353f5bbb74667aa375cb68bd24799
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846746B2
Reaction notes
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