Monoethyl malonate → HCID 54229279, compound

HRID 1108418Notes

Reaction equation

HRID 1108418 reaction equation
[O:1]1[C:9]2[C:4](=[N:5][C:6]([CH:10]=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:12]([O:18][CH2:19][CH3:20])(=[O:17])[CH2:13]C(O)=O.C([O-])(=O)C.[NH4+:25]>C(O)C>[CH2:19]([O:18][C:12](=[O:17])[CH2:13][CH:10]([NH2:25])[C:6]1[N:5]=[C:4]2[CH:3]=[CH:2][O:1][C:9]2=[CH:8][CH:7]=1)[CH3:20]

Participants

5

Reactant 3

HCID 70615Monoethyl malonateHCID 517165Ammonium AcetateHCID 10725492FURO[3,2-B]PYRIDINE-5-CARBOXALDEHYDE

Product 1

HCID 54229279HCID 54229279, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution containing aldehyde 23-2 (1.5 g, 10 mmol), ethyl hydrogen malonate (1.6 g, 20 mmol), and ammonium acetate (3.8 g, 50 mmol) in anhydrous ethanol (125 mL) was heated at reflux for 8 h. After cooling to room temperature, the solvent was evaporated and the residue partitioned between sat. sodium bicarbonate and EtOAc, the organic layer removed, dried, and concentrated. Chromatography of the residue afforded the amino ester 23-3 as a waxy solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 8 h
  3. customthe solvent was evaporated
  4. customthe residue partitioned between sat. sodium bicarbonate and EtOAc
  5. customthe organic layer removed
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-08960fa0ac954f828063feb5d06c4ad1
Source dataset
uspto-grants-2000_05
Patent number
US06066648

Reaction notes

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