Monoethyl malonate → HCID 54441812, compound

HRID 850633Notes

Reaction equation

HRID 850633 reaction equation
[O:1]1[C:5]2=[N:6][CH:7]=[C:8]([CH:10]=O)[CH:9]=[C:4]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:8]1[CH:9]=[C:4]2[CH:3]=[CH:2][O:1][C:5]2=[N:6][CH:7]=1)[CH3:20]

Participants

5

Reactant 3

HCID 70615Monoethyl malonateHCID 517165Ammonium AcetateHCID 10749327furo[2,3-b]pyridine-5-carbaldehyde

Product 1

HCID 54441812HCID 54441812, 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-5040458b951c433abc46dcedbaf49d2d
Source dataset
uspto-grants-2000_01
Patent number
US06017926

Reaction notes

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