Tri-o-tolylphosphine → HCID 22132398, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of palladium(II) acetate (0.112 g), tri-o-tolylphosphine (0.304 g), 3,4-ethylenedioxybromobenzene (1.075 g) and (±)-5-(pyridin-3-yl)-1-penten-3-ol (0.815 g, Example 1a)) in triethylamine (10 ml) in acetonitrile (30 ml) was heated at 80° C. for 3 hours and 30 minutes. The mixture was cooled to room temperature and filtered through Celite® and the filtrate concentrated under reduced pressure. The residue was redissolved in ethyl acetate and the solution washed with water then dried over anhydrous magnesium sulfate. The solution was then filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with hexane:acetone (3:1) then (2:1) to give firstly 1-(benzo-1,4-dioxan-6-yl)-5-(pyridin-3-yl)-3-pentanone as an oil (0.812 g) and secondly (±)-trans-1-(benzo-1,4-dioxan-6-yl)-5-(pyridin-3-yl)-pent-1-en-3-ol as an oil (0.252 g).

Provenance & Evidence