Isobutylene → Tert-butyl 5-oxotetrahydrofuran-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 5.0 g 5-oxo-2-tetrahydrofurancarboxylic acid in 100 ml dichloromethane 0.3 ml concentrated sulfuric acid and then an excess amount of isobutene (about 50 ml) were added, while maintaining the solution at -60° C. The reaction mixture was kept standing in a tightly seald flask at room temperature overnight, and thereafter it was poured into a cooled saturated aqueous solution of sodium bicarbonate, and the dichloromethane layer was separated. After washing with water and drying (over Na2SO4), the dichloromethane layer was concentrated to yield t-butyl 5-oxo-2- tetrahydrofurancarboxylate in the form of a colorless oily substance.

Provenance & Evidence