4-tert-Butylcatechol → HCID 22645397, compound

Participants

Reaction Steps

To a stirred solution of 1-hexanoyl-3,4-dimethyl-4-(trifluoromethanesulfonyloxyphenyl)piperidine (Preparation 6, 3.0 g, 6.90 mmol) in tetrahydrofuran (30 mL) at room temperature were added sequentially vinyltributyltin (2.12 mL, 7.24 mmol), lithium chloride (585 mg, 13.8 mmol), and tetrakis(triphenylphosphine)palladium(0) (80 mg, 0.69 mmol). The mixture was heated to reflux under a nitrogen atmosphere for 1½ hours at which time a few crystals of 4-tert-butylcatechol were added. Heating at reflux was then continued for a further 16 hours. The mixture was cooled and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a gradient of ethyl acetate:hexane (1:10 to 1:3). The title compound was obtained as a clear oil (2.1 g).

Provenance & Evidence