反应详情

To 133 g (1.31 mol) of tetrahydropyran-4-ol in pyridine (1.5 L) are added 373 g (1.95 mol) of p-toluenesulfonylchloride portionwise at 10° C. After complete addition the reaction is allowed to warm to RT and stirred for 18 h. The reaction is poured onto a stirred mixture of aq. HCl/ice. The resulting precipitate is isolated by filtration and dissolved in DCM (1 L). The organic layer is washed with 1 M aq. HCl solution (1 L), followed by sat. aq. NaHCO3 solution (1 L) and is then dried over Na2SO4. Filtration and concentration of the filtrate under reduced pressure gives 300 g of toluene-4-sulfonic acid tetrahydropyran-4-yl ester. Yield: 90%; ESI-MS: 257 [M+H]+

1. additionAfter complete addition the reaction
2. customThe resulting precipitate is isolated by filtration
3. washThe organic layer is washed with 1 M aq. HCl solution (1 L)
4. dry with materialis then dried over Na2SO4
5. filtrationFiltration and concentration of the filtrate under reduced pressure