Reaktion #65282

Reaktionsgleichung

2-butyl-5-hydroxymethyl-4-iodoimidazole

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product

Ausbeute 84.2%

2-butyl-4-iodoimidazol-5-carboxaldehyde

Ausbeute 84.2%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 24 hours
2. 2
   Sonstigeto remove water
3. 3
   FiltrationThe hot reaction mixture was filtered through Celite® which
4. 4
   Waschenwas then washed with 4.5 liters of boiling methylene chloride
5. 5
   EinengenThe combined filtrates were concentrated to dryness
6. 6
   workup.DISSOLUTIONthe residue was dissolved twice in 150 mL of methanol
7. 7
   Einengenthe solution was concentrated to dryness
8. 8
   workup.DISSOLUTIONThe residue was dissolved in 130 mL of methanol
9. 9
   Temperaturchilled
10. 10
    SonstigeAfter crystallization
11. 11
    workup.ADDITION700 mL of water was added slowly
12. 12
    TemperaturThe mixture was chilled
13. 13
    Filtrationthe solid was collected by filtration
14. 14
    Waschenwashed with water

Vorschrift

A stirred mixture of 174.1 g (0.62 mol) of 2-butyl-5-hydroxymethyl-4-iodoimidazole and 360 g (4.14 mol) of manganese dioxide in 3 liters of methylene chloride was refluxed for 24 hours using a trap to remove water. The hot reaction mixture was filtered through Celite® which was then washed with 4.5 liters of boiling methylene chloride. The combined filtrates were concentrated to dryness, the residue was dissolved twice in 150 mL of methanol and the solution was concentrated to dryness. The residue was dissolved in 130 mL of methanol and chilled. After crystallization had occurred, 700 mL of water was added slowly. The mixture was chilled, the solid was collected by filtration, and washed with water to give 145.2 g (84%) of product; mp 104°-105° C.

Quelle