Methyl iodide → HCID 20313171, compound

Participants

Reaction Conditions

Reaction Steps

n-Butyl lithium (8.15ml. of a 1.23M solution in hexane) was added dropwise to a stirred solution of di-isopropylamine (1.40ml.) in dry tetrahydrofuran (15ml.) at -78° C. in an atmosphere of argon. The solution was warmed to 0° C. and a solution of methyl 3-phenylcyclobutanecarboxylate (1.90g.) in dry tetrahydrofuran (20ml.) was added dropwise and the reaction mixture was stirred at 0° C. for 1 hour. Methyl iodide (1.30ml.) was added and stirring was continued for 16 hours, allowing the reaction mixture to warm to room temperature. The tetrahydrofuran was evaporated under reduced pressure and the residue was partitioned between ethyl acetate (2 × 20ml.) and 0.5N hydrochloric acid (10ml.). The ethyl acetate solution was dried over sodium sulphate and the solvent was evaporated under reduced pressure to give the ester, methyl 1-methyl-3-phenylcyclobutanecarboxylate as a 2:1 mixture of isomers. The n.m.r. spectrum is deuteriochloroform showed the following characteristic features (δ values):

Provenance & Evidence