Diethyl Oxalate → 2,4-Dioxo-5-phenoxy-pentanoic acid ethyl ester
Reaction equation
[Na].[O:2]([CH2:9][C:10](=[O:12])[CH3:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:13](OCC)(=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]>CCO>[CH2:17]([O:16][C:14](=[O:15])[C:13](=[O:19])[CH2:11][C:10](=[O:12])[CH2:9][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH3:18]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Sodium (6.74 g, 293 mmol) was added to EtOH (808 mL) at 0° C. The mixture was stirred at 0° C. until the sodium was completely dissolved. Then phenoxy-2-propanone (53 mL, 266 mmol) was added dropwise. The mixture was stirred at 0° C. for 10 minutes and then diethyl oxalate (36 mL, 266 mmol) was added. Then the mixture was stirred at room temperature for 16 hours and the solvent was evaporated in vacuo. The residue was dissolved in H2O and the mixture was acidified with a 1M solution of HCl and extracted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by open column chromatography (silica; DCM) to yield 2,4-dioxo-5-phenoxy-pentanoic acid ethyl ester (35.9 g, 54% yield) as an oil.
Workup
- dissolutionwas completely dissolved
- stirringThen the mixture was stirred at room temperature for 16 hours
- customthe solvent was evaporated in vacuo
- dissolutionThe residue was dissolved in H2O
- extractionextracted with DCM
- customThe organic layer was separated
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customthe solvents evaporated in vacuo
- customThe crude product was purified by open column chromatography (silica; DCM)
Sources & evidence
- ORD record
- ord-b8195e39ee5a45ee81fc19b7f782f4a6
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09255103B2
Reaction notes
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