Water → HCID 58452683, Verbindung

HRID 70719

Reaktionsgleichung

Reaktionsgleichung von HRID 70719
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([C:9]1[CH:14]=[CH:13][C:12]([CH:15](OCC2CCCC2)[C:16]2[N:21]=[C:20]([O:22]C)[C:19]([Cl:24])=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)([CH3:8])([CH3:7])[CH3:6].O.[CH:33]1([SH:38])[CH2:37][CH2:36][CH2:35][CH2:34]1>>[C:5]([C:9]1[CH:10]=[CH:11][C:12]([CH:15]([S:38][CH:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)[C:16]2[NH:21][C:20](=[O:22])[C:19]([Cl:24])=[CH:18][CH:17]=2)=[CH:13][CH:14]=1)([CH3:6])([CH3:7])[CH3:8]

Komponenten

5

Edukt 4

HCID 962WaterHCID 15510CyclopentanethiolHCID 6451240Aluminum(III) ChlorideHCID 673980526-[(4-Tert-butylphenyl)(cyclopentylmethoxy)methyl]-3-chloro-2-methoxypyridine

Produkt 1

HCID 58452683HCID 58452683, VerbindungAusbeute 25 %

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Aluminum chloride (66 mg) was added to a solution of 6-[(4-tert-butylphenyl)(cyclopentylmethoxy)methyl]-3-chloro-2-methoxypyridine (64 mg) in cyclopentanethiol (1 mL) under ice-cooling, and then the mixture was stirred at 40° C. for two hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was purified by preparative TLC (hexane:ethyl acetate=1:10) to give the title compound as a pale yellow solid (15 mg, 25%).

Aufarbeitung

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customafter which the solvent was evaporated under reduced pressure
  7. customThe residue was purified by preparative TLC (hexane:ethyl acetate=1:10)

Quellen und Nachweise

ORD-Eintrag
ord-647e824dcc404ac691cde1adf01144e7
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822503B2

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