4-Toluenesulfonyl chloride → HCID 66818580, compound

Participants

Reaction Steps

n-Butyllithium (2.6 M solution in hexane, 0.295 ml, 0.767 mmol) was added to a solution of 2-(9-benzyloxy-nonyl)-2-methyl-propane-1,3-diol (221 mg, 0.686 mmol) in THF (5.1 ml) at 0° C. over three minutes, and the mixture was then stirred at the same temperature for 30 minutes. A solution of TsCl (138 mg, 0.723 mmol) in THF (0.91 ml) was added to the reaction solution at 0° C. over eight minutes, and the mixture was then stirred at the same temperature for one hour. n-Butyllithium (2.6 M solution in hexane, 0.295 ml, 0.767 mmol) was added dropwise to the reaction mixture at 0° C., and the mixture was then stirred at 60° C. for six hours. The reaction mixture was diluted with ether and water was then added, followed by extraction with ether. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=15/1) to give 3-(9-benzyloxy-nonyl)-3-methyl-oxetane (188 mg, 90%).

Provenance & Evidence