1,4-Dioxane → HCID 89751832, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2,7-dibromo-4,5-dihydronaphtho[1,2-d]thiazole (4b) (1.7 g, 5.07 mmol) in 30 ml of anhydrous dioxane was degassed by passing nitrogen gas for 15 min. Tributyl(1-ethoxyvinyl)stannane (4.58 g, 12.68 mmol) was added to it followed by PdCl2(PPh3)2 (0.36 g, 0.51 mmol) and the solution was heated at 90° C. overnight. After cooling, the volume of dioxane was reduced and a saturated solution of KF was added to it and stirred for 15 min., after which the mixture was passed through a pad of celite and washed with ethyl acetate. The combined filtrate was stirred with 4 N HCl solution for 1 h and the organic layer was dried and concentrated and the residue was purified by column chromatography to obtain the diacetyl compound (4c) (1.37 g, 73%). m/z 271.0 (M+).

Provenance & Evidence