Reaktion #1092693

Reaktionsgleichung

1,1-dimethoxycycloheptane

compound 8

5-(3,5-Dichlorophenylthio)-4-isopropyl-1-[2-hydroxyethoxymethyl]-2-methyl-1H-imidazole

p-toluenesulfonic acid hydrate

toluene

→

compound 10

1-[2-(Cyclohepten-1-yloxy)ethoxymethyl]-5-(3,5-dichlorophenylthio)-4-isopropyl-2-methyl-1H-imidazole

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenwas concentrated under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in toluene (2 mL), to which
3. 3
   TemperaturThe reaction mixture was heated
4. 4
   Temperaturunder reflux over 1 hour
5. 5
   Einengenconcentrated to a small quantity
6. 6
   workup.ADDITIONA drop of triethylamine was added to the reaction mixture
7. 7
   Einengenthe mixture was concentrated under reduced pressure
8. 8
   workup.ADDITIONHexane was added
9. 9
   Filtrationthe mixture was filtered
10. 10
    Sonstigeto remove the insoluble matter
11. 11
    Sonstigethe filtrate was purified by chromatography on an alumina column (eluate: hexane - ethyl acetate (2:1))

Vorschrift

A solution of the compound 8 (450 mg, 1.20 mmol) and p-toluenesulfonic acid hydrate (20.0 mg, 0.105 mmol) in a mixture of methylene chloride (1 mL) - toluene (0.1 mL) was concentrated under reduced pressure. The residue was dissolved in toluene (2 mL), to which was added 1,1-dimethoxycycloheptane (1.51 g, 12.0 mmol). The reaction mixture was heated under reflux over 1 hour and concentrated to a small quantity. A drop of triethylamine was added to the reaction mixture, and the mixture was concentrated under reduced pressure. Hexane was added thereto, the mixture was filtered to remove the insoluble matter, and the filtrate was purified by chromatography on an alumina column (eluate: hexane - ethyl acetate (2:1)) to give the compound 10 (275 mg, 47%) as oil. Rf 0.64 (Al2O3 60, Type E, 2:1 hexane -EtOAc).

Quelle