Imidazole → 1-[4-(4-Benzyloxyphenyl)butyl]imidazole

HRID 322310Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 322310
CS(O[CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][CH:11]=1)(=O)=O.[NH:24]1[CH:28]=[CH:27][N:26]=[CH:25]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:17]([O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][CH2:8][CH2:7][CH2:6][N:24]2[CH:28]=[CH:27][N:26]=[CH:25]2)=[CH:11][CH:12]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 227333684-[4-(Benzyloxy)phenyl]butyl methanesulfonate

Produkt 1

HCID 220097591-[4-(4-Benzyloxyphenyl)butyl]imidazoleAusbeute 61,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 4-(4-benzyloxyphenyl)butyl methane sulfonate (25.0 g), imidazole (11.2 g), potassium carbonate (15.5 g) and N,N-dimethylformamide (200 ml) was stirred for 16 hours at 80° C. The reaction mixture was poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography. From the fraction eluted with ethyl acetate-methanol (20:1, v/v), 1-[4-(4-benzyloxyphenyl)butyl]imidazole (14.0 g, 61%) was obtained. Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 97-98° C.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. washFrom the fraction eluted with ethyl acetate-methanol (20:1

Quellen und Nachweise

ORD-Eintrag
ord-8733d8af17d14d5981364cd46b00b96c
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211215B1

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