Hydrochloric Acid → Ethyl 4-(furan-2-yl)-2,4-dioxobutanoate

HRID 33247

Reaction equation

HRID 33247 reaction equation
C(O[C:4](=[O:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6])C.CC([O-])(C)C.[K+].[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22](=[O:24])[CH3:23].Cl>C1COCC1.C(OCC)(=O)C.O>[CH2:8]([O:7][C:5](=[O:6])[C:4](=[O:10])[CH2:23][C:22]([C:18]1[O:17][CH:21]=[CH:20][CH:19]=1)=[O:24])[CH3:9]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 145052-AcetylfuranHCID 23665647Potassium tert-butoxide

Product 1

HCID 3006753Ethyl 4-(furan-2-yl)-2,4-dioxobutanoate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 16 g oxalic acid diethyl ester in 350 ml THF, 10.1 g KOt-Bu were added at 0° C. Then 10 g 1-furan-2-yl-ethanone in 50 ml THF were added dropwise. After 1 h the reaction mixture was diluted with 300 ml ethyl acetate and 200 mnl water. This solution was acidified with diluted hydrochloric acid to pH 5. The organic layer was separated, washed with 150 ml water, dried over MgSO4, filtered and concentrated under reduced pressure to yield a white solid.

Workup

  1. customThe organic layer was separated
  2. washwashed with 150 ml water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto yield a white solid

Sources & evidence

ORD record
ord-4c8badb3b96b4d3aa4e6dc9d0f230fe0
Source dataset
uspto-grants-2008_09
Patent number
US07429581B2

Linked notes

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