1,4-Dioxane → HCID 10134858, compound

Participants

Reaction Conditions

Reaction Steps

In dioxane was placed 4-bromo-1,3-benzenedicarboxylate dibenzyl ester (1.78 g, 4.2 mmol), tri-n-butyl(1-ethoxyvinyl), tin (1.70 g, 4.7 mmol), and bis-triphenylphosphine palladium (II) dichloride (175 mg, 0.25 mmol). The mixture was warmed to 100° C. and stirred for 24 hours. The dark solution was evaporated at reduced pressure to give an oil. The oil was purified by MPLC (90 g silica gel, 3:1 [hexane:ethyl acetate]). This gave 0.91 g of the ethoxyvinyl intermediate. This was then placed into a solution of acetic acid (25 mL) and water (5%) and stirred for 1 hour. The mixture was evaporated in vacuo to give an oil which was purified by MPLC (90 g silica gel, 8:2 [hexane:ethyl acetate]). This gave 699 mg (43%) of a white solid. MS: M+1=389.2.

Provenance & Evidence