Diethyl Oxalate → 2,4-Dioxo-5-phenoxy-hexanoic acid ethyl ester

HRID 2046180

Reaction equation

[Na].[O:2]([CH:9]([CH3:13])[C:10](=[O:12])[CH3:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:14](OCC)(=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16]>CCO>[CH2:18]([O:17][C:15](=[O:16])[C:14](=[O:20])[CH2:11][C:10](=[O:12])[CH:9]([O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH3:13])[CH3:19]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium (82 mg, 3.55 mmol) was added to EtOH absolute (9.8 mL) at 0° C. The mixture was stirred at 0° C. until the sodium was completely dissolved. Then (rac)-3-phenoxy-butan-2-one (530 mg, 3.23 mmol) was added dropwise. The mixture was stirred at 0° C. for 10 minutes. Then diethyl oxalate (0.44 mL, 3.23 mmol) was added. Then the mixture was stirred at room temperature for 16 hours and the solvent evaporated in vacuo. The residue was diluted with water, the mixture 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 100%) to yield (rac)-2,4-dioxo-5-phenoxy-hexanoic acid ethyl ester (566 mg, 58% yield) as an orange oil.

Workup

dissolutionwas completely dissolved
stirringThen the mixture was stirred at room temperature for 16 hours
customthe solvent evaporated in vacuo
additionThe residue was diluted with water
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 100%)

Sources & evidence

ORD record: ord-69f8725c59d1439fa42b0bbbcabbe8db
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592422B2

Linked notes

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