Monoethyl malonate → HCID 54229279, compound

HRID 850635Notes

Reaction equation

HRID 850635 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 24-2 (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 24-3 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-da2bbf04948c4d4db621fda416d880e2
Source dataset
uspto-grants-2000_01
Patent number
US06017926

Reaction notes

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