Chloroacetyl chloride → Ethyl 2-ethoxy-4-oxo-4,5-dihydrofuran-3-carboxylate

HRID 402640Notes

Reaction equation

HRID 402640 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].Cl[CH2:15][C:16](Cl)=[O:17]>O1CCCC1.O>[CH2:10]([O:9][C:1]1[O:8][CH2:15][C:16](=[O:17])[C:2]=1[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH3:11]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 7761Diethyl MalonateHCID 24758Sodium hydride

Product 1

HCID 13791062Ethyl 2-ethoxy-4-oxo-4,5-dihydrofuran-3-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Diethyl malonate (8.0 mL, 0.052 mol) was added dropwise to a solution of sodium hydride (60% w/w in oil, 4.2 g, 0.11 mol) in anhydrous tetrahydrofuran (130 mL) that cooled with ice bath. The mixture was refluxed for 7 min. The reaction mixture was cooled with ice bath, chloroacetyl chloride (4.2 mL, 0.052 mol) was added dropwise to the reaction mixture and stirred for 1 h then stirred at 45° C. for 1 h. Cooled to ambient temperature, the reaction mixture was diluted with water, and extracted with chloroform for 4 times. The organic layer was dried over magnesium sulfate and concentrated. The residue was purified by chromatography on silica gel(chloroform/methanol) to afford ethyl 2-ethoxy-4-oxo-4,5-dihydrofuran-3-carboxylate as solid (5.0 g, y. 48%).

Workup

  1. temperaturecooled with ice bath
  2. temperatureThe mixture was refluxed for 7 min
  3. temperatureThe reaction mixture was cooled with ice bath
  4. stirringthen stirred at 45° C. for 1 h
  5. extractionextracted with chloroform for 4 times
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel(chloroform/methanol)

Sources & evidence

ORD record
ord-9be5c1286b684fd2aac57b5c1546e169
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

Loading…