Hydrochloric Acid → HCID 69950472, compound

HRID 1656447Notes

Reaction equation

HRID 1656447 reaction equation
[C:1](OCC)(=O)[CH2:2][C:3]([OH:5])=[O:4].[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH:15]=O.[C:17]([O-])(=O)C.[NH4+:21].Cl>C(O)C.CCOCC>[C:3]([O:5][C:12]1([NH2:21])[CH:13]=[CH:14][O:10][CH:11]1[CH2:15][CH3:17])(=[O:4])[CH2:2][CH3:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7362FurfuralHCID 70615Monoethyl malonateHCID 517165Ammonium Acetate

Product 1

HCID 69950472HCID 69950472, compoundYield 31.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Ethyl hydrogen malonate (13.7 g, 104 mmol) was added to 2-furanal (10 g, 104 mmol) and ammonium acetate (20 g, 260 mmmol) in dry ethanol. The solution was heated to reflux for 6 h. The solvent was removed in vacuo to leave an oil. To this oil, 10% HCl (250 mL) was added along with ether (100 mL). The layers were separated, extracted twice with methylene chloride, dried over Na2SO4, and the solvent removed in vacuo to give 6 g of the title compound.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 6 h
  3. customThe solvent was removed in vacuo
  4. customto leave an oil
  5. customThe layers were separated
  6. extractionextracted twice with methylene chloride
  7. dry with materialdried over Na2SO4
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-d801f50c0837457b985ed591ed14a6f2
Source dataset
uspto-grants-1993_10
Patent number
US05254573

Reaction notes

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