3-Bromobut-1-ene → (E)-5-bromo-1-(3,3-diethoxypropoxy)-2-methylpent-2-ene

Participants

Reaction Steps

To previously nitrogen degassed DCM (18 mL) was added Second Generation Grubbs Catalyst (0.225 g, 0.30 mmol) followed by 3-bromobutene (2.03 g, 15.0 mmol) and 3-(3,3-diethoxypropoxy)-2-methylprop-1-ene (1.52 g, 7.52 mmol). The reaction mixture was further degassed for 5 minutes and then heated under reflux for 2 hours. The solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography eluting with 0-100% ethyl acetate in iso-hexane to afford the title compound (0.208 g, 9%).

Provenance & Evidence