Hydrochloric Acid → HCID 21862807, Verbindung

HRID 1415823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1415823
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:24]=[CH:23][C:8]([C:9](=[O:22])[CH2:10][CH:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=1.[CH:25]1([O:30][C:31]2[CH:32]=[C:33]([CH:36]=[CH:37][C:38]=2[O:39][CH3:40])[CH2:34]Cl)[CH2:29][CH2:28][CH2:27][CH2:26]1.[I-].[Na+].Cl>O1CCCC1>[CH:25]1([O:30][C:31]2[CH:32]=[C:33]([CH:36]=[CH:37][C:38]=2[O:39][CH3:40])[CH2:34][C:11]([CH2:10][C:9]([C:8]2[CH:7]=[CH:6][C:5]([O:4][CH3:3])=[CH:24][CH:23]=2)=[O:22])([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:26][CH2:27][CH2:28][CH2:29]1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 109007664-(Chloromethyl)-2-(cyclopentyloxy)-1-methoxybenzeneHCID 21862838Diethyl alpha-(4-methoxyphenacyl)malonate

Produkt 1

HCID 21862807HCID 21862807, VerbindungAusbeute 73,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

0.29 g (7.1 mmol) of sodium hydride (as a 60% w/w dispersion in mineral oil) was added to 50 ml of anhydrous tetrahydrofuran, whilst ice-cooling, and then the mixture was stirred for 10 minutes. At the end of this time, a solution of 2.00 g (6.5 mmol) of diethyl α-(4-methoxyphenacyl)malonate [prepared as described in step (i) above] in 20 ml of anhydrous tetrahydrofuran was slowly added dropwise to the mixture, whilst ice-cooling. The mixture was then stirred for 30 minutes. A solution of 1.72 g (7.1 mmol) of 3-cyclopentyloxy-4-methoxybenzyl chloride in 20 ml of anhydrous tetrahydrofuran and 0.97 g (6.5 mmol) of sodium iodide were then added to the mixture, and the resulting mixture was heated under reflux for 2 hours. At the end of this time, the mixture was cooled to room temperature and was then acidified by the addition of 3N aqueous hydrochloric acid and extracted with ethyl acetate. The organic extract was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was removed by distillation under reduced pressure. The residue thus obtained was applied to a silica gel chromatography column and eluted with a 1:4 by volume mixture of ethyl acetate and hexane, to give 2.45 g of the title compound as a pale yellow oily substance.

Aufarbeitung

  1. temperaturecooling
  2. temperaturecooling
  3. stirringThe mixture was then stirred for 30 minutes
  4. temperaturethe resulting mixture was heated
  5. temperatureunder reflux for 2 hours
  6. extractionextracted with ethyl acetate
  7. extractionThe organic extract
  8. washwas washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was removed by distillation under reduced pressure
  11. customThe residue thus obtained
  12. washeluted with a 1:4 by volume mixture of ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-41a85c9f7caa4c20adae9a0551242690
Quelldatensatz
uspto-grants-1999_06
Patentnummer
US05908858

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