Reaktion #43431

Reaktionsgleichung

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

sodium periodate

→

solid

Ausbeute 36.0%

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

Ausbeute 36.0%

Lösungsmittel

1,4-dioxane water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter 2.5 hours the mixture was evaporated to dryness
2. 2
   workup.DISSOLUTIONdissolved in 1,4-dioxane
3. 3
   workup.ADDITIONSilica gel was added
4. 4
   Sonstigethe mixture was evaporated to dryness
5. 5
   workup.ADDITIONadded to a silica column (50 g)
6. 6
   Sonstigechromatographed
7. 7
   Wascheneluting with 0-100% ethyl acetate in hexane

Vorschrift

A solution of 3-ethenyl-6,7-dihydro[1,4]oxathiino[2,3-c]pyridazine (320 mg) in 1,4-dioxane/water (20 ml/5 ml) was treated with an aqueous solution of osmium tetroxide (4% w/v, 2 ml) and sodium periodate (1.08 g), initially stirred in an ice-bath, then allowed to warm to room temperature. After 2.5 hours the mixture was 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 (50 g) and chromatographed, eluting with 0-100% ethyl acetate in hexane, to afford a white solid (116 mg, 36%).

Quelle