Reaktion #43432

Reaktionsgleichung

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

potassium carbonate

2,4,6-trivinylcyclotriboroxane pyridine complex

water

→

solid

Ausbeute 71.2%

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

Ausbeute 71.2%

Lösungsmittel

dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was evaporated to dryness
2. 2
   workup.ADDITIONtreated with aqueous sodium bicarbonate solution
3. 3
   Extraktionextracted (4×) with DCM
4. 4
   Trocknendried (sodium sulphate)
5. 5
   Sonstigeevaporated
6. 6
   Sonstigechromatographed on silica gel (50 g)
7. 7
   Wascheneluting with 1:1 ethyl acetate-hexane

Vorschrift

A solution of 3-chloro-6,7-dihydro[1,4]oxathiino[3,2-c]pyridazine (450 mg, 2.4 mmol) in dimethoxyethane (12 ml) was treated with tetrakis(triphenylphosphine)palladium (0) (61 mg), potassium carbonate (313 mg), 2,4,6-trivinylcyclotriboroxane pyridine complex (375 mg) and water (1.5 ml). The mixture was heated at 96° C., overnight. The mixture was evaporated to dryness, treated with aqueous sodium bicarbonate solution, extracted (4×) with DCM, dried (sodium sulphate), evaporated and chromatographed on silica gel (50 g), eluting with 1:1 ethyl acetate-hexane, affording a solid (200 mg, 46%), containing slightly impure product.

Quelle