Réaction #43450

Équation de réaction

sodium periodate

3-ethenyl-6,7-dihydro[1,4]dioxino[2,3-c]pyridazine

→

solid

Rendement 64.4%

6,7-Dihydro[1,4]dioxino[2,3-c]pyridazine-3-carbaldehyde

Rendement 64.4%

Solvants

1,4-dioxane water

Conditions de réaction

Traitement

1. 1
   Autrewas evaporated to dryness
2. 2
   Autreazeotroped with 1,4-dioxane
3. 3
   workup.ADDITIONSilica gel, 1,4-dioxane and chloroform were added
4. 4
   Autrethe mixture was evaporated to dryness overnight
5. 5
   workup.ADDITIONadded to a silica column (400 g)
6. 6
   Autrechromatographed
7. 7
   Lavageeluting with chloroform

Mode opératoire

A solution of 3-ethenyl-6,7-dihydro[1,4]dioxino[2,3-c]pyridazine (11.58 g) in 1,4-dioxane/water (600 ml/180 ml), cooled in ice, was treated with an aqueous solution of osmium tetroxide (4% w/v, 25 ml) and sodium periodate (43 g). This mixture was allowed to warm to room temperature and after 7 hours under stirring the mixture was evaporated to dryness and azeotroped with 1,4-dioxane. Silica gel, 1,4-dioxane and chloroform were added and the mixture was evaporated to dryness overnight, then added to a silica column (400 g) and chromatographed, eluting with chloroform then 0-100% ethyl acetate in hexane, to afford a white solid (7.55 g, 64%).

Source