Dimethylacetamide → tert-butyl 4-((E)-2-(2,3-dihydrobenzo[1,4]dioxin-6-yl)vinyl)-2-nitrobenzoate

Participants

Reaction Conditions

Reaction Steps

To N,N-dimethylacetamide 24 mL solution of tert-butyl 4-bromo-2-nitrobenzoate 3.0 g were added 2,3-dihydro-6-vinylbenzo[1,4]dioxin 2.4 g, N,N-dicyclohexylmethylamine 4.0 mL and palladium acetate 0.11 g at room temperature, and it was stirred under nitrogen atmosphere at 120° C. for 3 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and water were added to it, and insoluble matter was filtrated. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with 10% citric acid aqueous solution and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B(spherical type), eluent; hexane:ethyl acetate=10:1] to give tert-butyl 4-((E)-2-(2,3-dihydrobenzo[1,4]dioxin-6-yl)vinyl)-2-nitrobenzoate 1.5 g of yellow solid.

Provenance & Evidence