Trichloroacetyl chloride → HCID 54546861, Verbindung

HRID 1654524

Reaktionsgleichung

Reaktionsgleichung von HRID 1654524
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14](=[CH2:17])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:18][C:19](Cl)([Cl:23])[C:20](Cl)=O.P(Cl)(Cl)(Cl)=[O:26]>CCOCC.[Cu].[Zn]>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14]2([C:19]([Cl:23])([Cl:18])[CH2:20][C:17]2=[O:26])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 6420Trichloroacetyl chlorideHCID 24813Phosphorus oxychlorideHCID 15519136Benzyl 4-methylidenepiperidine-1-carboxylate

Produkt 1

HCID 54546861HCID 54546861, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10290809Zinc copper coupleKatalysatorHCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 1-benzyloxycarbonyl-4-methylenepiperidine (11.1 g, 49.3 mmol) and zinc-copper couple (95: 5, 7.98 g, 12.2 mmol) in 200 ml of anhydrous ether was added a solution of trichloroacetyl chloride (10.18 ml, 91.2 mmol) and phosphorous oxychloride (8.77 ml, 94.0 mmol) in 50 ml of anhydrous ether. The reaction mixture was refluxed overnight. After cooling to room temperature, the solution was filtered through celite and the filtrate was washed with brine and cold sodium bicarbonate, dried over magnesium sulfate and upon evaporation afforded the title compound as a yellow liquid, 15.3 g (crude).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed overnight
  2. filtrationthe solution was filtered through celite
  3. washthe filtrate was washed with brine and cold sodium bicarbonate
  4. dry with materialdried over magnesium sulfate and upon evaporation

Quellen und Nachweise

ORD-Eintrag
ord-f93c6ca023284b8aaa1e21fb81539071
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05407943

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