Réaction #43433

Équation de réaction

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

sodium periodate

sodium bicarbonate

→

solid

Rendement 31.2%

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

Rendement 31.2%

Solvants

1,4-dioxane water

Conditions de réaction

Traitement

1. 1
   Autreevaporated to dryness
2. 2
   workup.DISSOLUTIONdissolved in 1,4-dioxane
3. 3
   workup.ADDITIONSilica gel was added
4. 4
   Autrethe mixture was evaporated to dryness
5. 5
   workup.ADDITIONadded to a silica column (20 g)
6. 6
   Autrechromatographed
7. 7
   Lavageeluting with 0-100% ethyl acetate in hexane

Mode opératoire

A solution of 3-ethenyl-6,7-dihydro[1,4]oxathiino[3,2-c]pyridazine (200 mg, 1.11 mmol) in 1,4-dioxane/water (10 ml/2 ml) was treated with an aqueous solution of osmium tetroxide (4% w/v, 1 ml) and sodium periodate (0.55 g), initially stirred in an ice-bath for 1.5 hours, then allowed to warm to room temperature. After 1.5 hours the mixture was treated with sodium bicarbonate solution, evaporated to dryness and dissolved in 1,4-dioxane and chloroform. Silica gel was added and the mixture was evaporated to dryness, added to a silica column (20 g), and chromatographed, eluting with 0-100% ethyl acetate in hexane, to afford a pale yellow solid (63 mg, 31%).

Source