Tri-o-tolylphosphine → HCID 22132398, compound

Temperature

80 °C

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).

1. temperatureThe mixture was cooled to room temperature
2. filtrationfiltered through Celite®
3. concentrationthe filtrate concentrated under reduced pressure
4. dissolutionThe residue was redissolved in ethyl acetate
5. washthe solution washed with water
6. dry with materialthen dried over anhydrous magnesium sulfate
7. filtrationThe solution was then filtered
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by column chromatography over silica eluting with hexane:acetone (3:1)

ORD record

ord-29f913015d1e467fabab1b28a67e44cd

Source dataset

uspto-grants-2000_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06143751