Reaktion #2442

Reaktionsgleichung

2-n-butyl-5-hydroxymethyl-4-iodoimidazole

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product

Ausbeute 84.2%

2-Butyl-4-iodoimidazole-5-carboxaldehyde

Ausbeute 84.2%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 24 hr
2. 2
   Sonstigeto remove water
3. 3
   FiltrationThe hot reaction mixture was filtered through a Celite® pad which
4. 4
   Waschenwas then washed with 4.5 L 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
   Einengeneach time the 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
15. 15
    Sonstigedried

Vorschrift

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

Quelle