Tetrabutylammonium Fluoride → 4-Ethynyl-3-(1-hydroxyethyl)azetidin-2-one

Participants

Reaction Steps

To a solution of 578 mg (2.74 mmol) of 3-(1-hydroxyethyl)-4-(2-trimethylsilylethynyl)-2-azetidinone, which was prepared according to T. Chiba and T. Nakai [Chem. Lett., 651 (1985)], in 5 ml of THF, 4 ml (4 mmol) of a 1M solution of tetrabutylammonium fluoride in THF was added. After stirring at room temperature for 2 hours, 10 g of silica-gel was added, the solvent was distilled away and the resultant was eluted with diethyl ether. The eluent was concentrated and purified with 10 g of silica-gel column (diethyl ether) to give 347 mg of 4-ethynyl-3-(1-hydroxyethyl)-2-azetidinone (yield: 92%).

Provenance & Evidence