Tetrahydrofuran → N-[2-t-Butyl-5-(2-cyclohexyl-1-hydroxyethyl)phenyl]-2-(9H-xanthen-9-yl)acetamide

HRID 1734864Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1734864
O1CCCC1.[C:6]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]=[O:17])=[CH:12][C:11]=1[NH:18][C:19](=[O:35])[CH2:20][CH:21]1[C:34]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:28][C:27]2[C:22]1=[CH:23][CH:24]=[CH:25][CH:26]=2)([CH3:9])([CH3:8])[CH3:7].[CH:36]1([CH2:42][Mg]Br)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1>C(OCC)C>[C:6]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]([OH:17])[CH2:42][CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)=[CH:12][C:11]=1[NH:18][C:19](=[O:35])[CH2:20][CH:21]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=2[O:28][C:29]2[C:34]1=[CH:33][CH:32]=[CH:31][CH:30]=2)([CH3:9])([CH3:7])[CH3:8]

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 19966116N-(2-t-butyl-5-formylphenyl)-2-(9H-xanthen-9-yl)acetamideHCID 178419664HCID 178419664, Verbindung

Produkt 1

HCID 19966142N-[2-t-Butyl-5-(2-cyclohexyl-1-hydroxyethyl)phenyl]-2-(9H-xanthen-9-yl)acetamideAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

8 ml of a tetrahydrofuran solution containing 100 mg (0.25 mmol) of N-(2-t-butyl-5-formylphenyl)-2-(9H-xanthen-9-yl)acetamide (prepared as described in Preparation 15) were cooled in an ice bath. 0.38 ml (0.38 mmol) of a 1M solution of cyclohexylmethylmagnesium bromide in diethyl ether was then added dropwise to the solution. The resulting mixture was stirred for 20 minutes at this temperature. It was then diluted with diethyl ether, and washed with dilute aqueous hydrochloric acid and then with water. The solvent was then removed by distillation under reduced pressure. The resulting residue was subjected to column chromatography through 20 g of silica gel. Elution with mixtures of methylene chloride and ethyl acetate ranging from 7:1 to 2:1 by volume afforded 95 mg (yield 76%) of the title compound as a foam-like substance.

Aufarbeitung

  1. temperaturewere cooled in an ice bath
  2. washwashed with dilute aqueous hydrochloric acid
  3. customThe solvent was then removed by distillation under reduced pressure
  4. washElution with mixtures of methylene chloride and ethyl acetate ranging from 7:1 to 2:1 by volume

Quellen und Nachweise

ORD-Eintrag
ord-b8be42c75ab84edd929100695eacb2de
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05534529

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