Diethyl Oxalate → HCID 12620579, Verbindung

HRID 1448891Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1448891
[Na].[CH3:2][C:3]([C:5]1[N:6]([CH3:15])[C:7]2[C:12]([C:13]=1[OH:14])=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4].[C:16](OCC)(=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(O)C>[CH3:15][N:6]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=2[C:13]2[O:14][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:2][C:3](=[O:4])[C:5]1=2

Komponenten

5

Edukt 3

HCID 7268Diethyl OxalateHCID 47121911-(3-hydroxy-1-methyl-1H-indol-2-yl)ethanoneHCID 5360545Sodium

Produkt 1

HCID 12620579HCID 12620579, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 6.0 g (0.26 mole) of sodium metal in 600 ml ab. ethanol was added 18.0 g (0.095 mole) of 3-hydroxy-1-methyl-1H-indol-2-yl methyl ketone, followed by 37.6 g (0.26 mole) of diethyl oxalate, added over 10 min. The mixture was stirred and heated at reflux for 17 hours, cooled and the red di-sodium salt was filtered and washed with cold hexane. The crude salt was added to a solution of 28 ml conc. HCl and 120 ml ab. ethanol, heated at reflux for 30 min., and the mixture was filtered while hot. Cooling the filtrate gave the crude product, which was filtered and then dissolved in 400 ml of chloroform. The chloroform solution was washed 3 times with dilute aqueous NaHCO3, 1 time with water, dried (MgSO4) and evaporated to leave a grey residue. Recrystallization from 15% CHCl3 in hexane gave yellow needles of mpt. 160°-162°.

Aufarbeitung

  1. additionadded over 10 min
  2. temperatureheated
  3. temperatureat reflux for 17 hours
  4. temperaturecooled
  5. filtrationthe red di-sodium salt was filtered
  6. washwashed with cold hexane
  7. additionThe crude salt was added to a solution of 28 ml conc. HCl and 120 ml ab
  8. temperatureethanol, heated
  9. temperatureat reflux for 30 min.
  10. filtrationthe mixture was filtered while hot
  11. temperatureCooling the filtrate

Quellen und Nachweise

ORD-Eintrag
ord-222d72b8bb9140bdbbef3145b70e0ac8
Quelldatensatz
uspto-grants-1980_02
Patentnummer
US04188326

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