Réaction #43429

Équation de réaction

3-ethenyl-6,7-dihydro-5H-pyrano[2,3-c]pyridazine

water

sodium periodate

→

product

Rendement 54.3%

6,7-Dihydro-5H-pyrano[2,3-c]pyridazine-3-carbaldehyde

Rendement 54.3%

Solvants

—

ice water

1,4-dioxane

Conditions de réaction

Traitement

1. 1
   Autrethe solvent was evaporated
2. 2
   workup.ADDITION1,4-Dioxane was added
3. 3
   Autreevaporated
4. 4
   Autrethe mixture briefly held in an ultrasonic bath
5. 5
   Lavageeluted with ethyl acetate

Mode opératoire

A solution of 3-ethenyl-6,7-dihydro-5H-pyrano[2,3-c]pyridazine (100 mg, 0.617 mmol) in 1,4-dioxane (5.5 ml)/water (1.1 ml) was cooled in ice/water and treated with sodium periodate (306 mg, 1.43 mmol) and a 4% aqueous solution of osmium tetroxide (0.55 ml). The mixture was allowed to warm to room temperature after an hour, and after a total of 4.75 hours stirring, the solvent was evaporated. 1,4-Dioxane was added and evaporated, followed by dichloromethane and the mixture briefly held in an ultrasonic bath. The whole mixture was applied to a silica gel column and eluted with ethyl acetate to give product (55 mg, 54%).

Source