Reaktion #43457

Reaktionsgleichung

water

potassium carbonate

2,4,6-trivinylcyclotriboroxane pyridine complex

5,6-dihydrofuro[2,3-c]pyridazin-3-yl trifluoromethanesulfonate

→

3-Ethenyl-5,6-dihydrofuro[2,3-c]pyridazine

Lösungsmittel

dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigefor a preparation of this reagent
2. 2
   Sonstigethen partitioned between DCM and saturated aqueous sodium bicarbonate solution
3. 3
   ExtraktionThe aqueous phase was extracted with 10% methanol in DCM
4. 4
   Sonstigethe combined organic extracts dried
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe residue was chromatographed
7. 7
   Wascheneluting with ethyl acetate affording a white solid (111 mg, 36%)

Vorschrift

A solution of 5,6-dihydrofuro[2,3-c]pyridazin-3-yl trifluoromethanesulfonate (500 mg, 1.85 mmol) in dimethoxyethane (20 ml) was degassed then treated with tetrakis(triphenylphosphine)palladium (0) (116 mg), potassium carbonate (257 mg), 2,4,6-trivinylcyclotriboroxane pyridine complex (for a preparation of this reagent see F. Kerins and D. F. O'Shea, J. Org. Chem. 2002, 67, 4968-4971) (416 mg) and water (3.6 ml). The mixture was stirred at 80° C. for 2 hours then partitioned between DCM and saturated aqueous sodium bicarbonate solution. The aqueous phase was extracted with 10% methanol in DCM then the combined organic extracts dried and evaporated. The residue was chromatographed eluting with ethyl acetate affording a white solid (111 mg, 36%).

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