Hydrochloric Acid → HCID 9990260, compound

HRID 584370Notes

Reaction equation

HRID 584370 reaction equation
[H-].[Na+].[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8](=[O:17])[CH2:9][C:10](OC(C)(C)C)=O.BrC[C:20]([O:22][CH2:23][CH3:24])=[O:21].Cl.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>O1CCCC1.C1(C)C=CC=CC=1.C(OCC)(=O)C.CCCCCC>[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8](=[O:17])[CH2:9][CH2:10][C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 10104541HCID 10104541, compound

Product 1

HCID 9990260HCID 9990260, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Sodium hydride (60% in oil, 629 mg) was added to a solution of tert-butyl 3-(2-furyl)-3-oxopropionate (3.01 g) in tetrahydrofuran (80 ml) at 0° C. and stirred for 10 minutes. Ethyl bromoacetate (1.51 ml) was added to the mixture, and then the reaction mixture was stirred at room temperature for 4 hours, 0.1N hydrochloric acid (200 ml) was added and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain an oil from an ethyl acetate-hexane (1:5, v/v)-eluted fraction. This was dissolved in toluene (150 ml), and trifluoroacetic acid (2.64 ml) was added, and then the reaction mixture was stirred at 90° C. for 6 hours. An aqueous saturated solution of sodium bicarbonate was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain ethyl 4-(2-furyl)-4-oxobutyrate (2.22 g, yield 79%) as a colorless oil from an ethyl acetate-hexane (1:3, v/v)-eluted fraction.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 4 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto obtain an oil from an ethyl acetate-hexane (1:5, v/v)-eluted fraction
  7. stirringthe reaction mixture was stirred at 90° C. for 6 hours
  8. extractionextracted with ethyl acetate
  9. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-2b1822d1280047a5aedf1fffdef4e21f
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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