As part of a project to prepare homologues of a drug, 2-Methyltetrahydrofuran was reacted with HBr for a ring opening to give a hydroxyl at one end and bromine at the other. However these products readily dibrominated and any of the free alcohol compounds left recyclized on contact with silica. Therefore acetic anhydride was added to the reaction and the ring opened product thus immediately acylated. The two products obtained (drawn below) were viewable by NMR in what looked like an 80:20 ratio. The mixture had a fruity, apple-like aroma, with a distinct C-Br bond smell that was absent in the 2-MeTHF start material which smelled minty/ethereal.
This project was abandoned to focus on other pursuits, but if I revisit it I'd like to try dry column vacuum chromatography (DCVC) to separate the compounds. While they looked to be separable it must be remembered that each spot is a racemic mixture of two compounds as a chiral centre has been created at the point on the alkyl chain with the methyl group.