3-Furaldehyde → HCID 11367399, compound

HRID 378131Notes

Reaction equation

HRID 378131 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH:6]=O)=[CH:2]1.[CH2:8]([O:10][C:11](=[O:16])[CH2:12]C(O)=O)[CH3:9].C([O-])(=O)C.[NH4+:21]>C(O)(C)C>[NH2:21][CH:6]([C:3]1[CH:4]=[CH:5][O:1][CH:2]=1)[CH2:12][C:11]([O:10][CH2:8][CH3:9])=[O:16]

Participants

5

Reactant 3

HCID 103513-FuraldehydeHCID 70615Monoethyl malonateHCID 517165Ammonium Acetate

Product 1

HCID 11367399HCID 11367399, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A suspension of 3-furancarboxaldehyde (8.6 ml), malonic acid monoethyl ester (15.8 g) and ammonium acetate (9.6 g) in isopropyl alcohol (200 ml) was heated to reflux under nitrogen. After 5 hours, the excess solvent was removed under reduced pressure and the semi-solid was treated with H2O (250 ml) and acidified to pH 2 using 12N HCl. The aqueous layer was washed with CH2Cl2 (2×100 ml). The aqueous layer was neutralized to pH>9 with K2CO3. The product was extracted with CH2Cl2 (2×100 ml). The organic layer was dried over Na2SO4 and the excess solvent was removed under reduced pressure to give ethyl β-aminofuran-3-propanoate (5 g) as a golden oil. The MS and 1H-NMR were consistent with the desired product.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen
  3. customthe excess solvent was removed under reduced pressure
  4. additionthe semi-solid was treated with H2O (250 ml)
  5. washThe aqueous layer was washed with CH2Cl2 (2×100 ml)
  6. extractionThe product was extracted with CH2Cl2 (2×100 ml)
  7. dry with materialThe organic layer was dried over Na2SO4
  8. customthe excess solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fab5310c149540ae8717359e584a2d96
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Reaction notes

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