반응 #2442

반응 방정식

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

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product

수율 84.2%

2-Butyl-4-iodoimidazole-5-carboxaldehyde

수율 84.2%

용매

dichloromethane

반응 조건

후처리

1. 1
   온도was refluxed for 24 hr
2. 2
   기타to remove water
3. 3
   여과The hot reaction mixture was filtered through a Celite® pad which
4. 4
   세척was then washed with 4.5 L of boiling methylene chloride
5. 5
   농축The combined filtrates were concentrated to dryness
6. 6
   workup.DISSOLUTIONThe residue was dissolved twice in 150 ml of methanol
7. 7
   농축each time the solution was concentrated to dryness
8. 8
   workup.DISSOLUTIONThe residue was dissolved in 130 ml of methanol
9. 9
   온도chilled
10. 10
    기타After crystallization
11. 11
    workup.ADDITION700 ml of water was added slowly
12. 12
    온도The mixture was chilled
13. 13
    여과the solid was collected by filtration
14. 14
    세척washed with water
15. 15
    기타dried

실험 절차

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.

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