Methanol → HCID 86743200, compound

Participants

Reaction Steps

A solution of cesium fluoride (0.05 g) in water (3 ml) is added to a mixture of 3-(1-hydroxy-1-methylethyl)-4-trimethylsilylethynyl-2-azetidinone (0.143 g) (cis-trans mixture), tetrahydrofuran (10 ml) and methanol (3 ml). The mixture is refluxed for 0.5 hour and then poured into a mixture of ethyl acetate (100 ml and water (50 ml). The organic layer is separated, washed with aqueous sodium chloride and dried over magnesium sulfate, followed by removal of the solvent by distillation under reduced pressure. The residue is subjected to silica gel column chromatography (eluent: 30-40% ethyl acetate/60-70% hexane). The first fraction gives 0.04 g of trans-3-(1-hydroxy-1-methylethyl)-4-ethynyl-2-azetidinone.

Provenance & Evidence