Реакция #50178

Уравнение реакции

4-methoxy-4-[3-(tetrahydropyran-2-yloxy)-prop-1-ynyl]tetrahydropyran

pyridinium p-toluenesulfonate

→

4-methoxy-4-(3-hydroxyprop-1-ynyl)tetrahydropyran

Выход 47.6%

Растворители

methanol

Условия реакции

Обработка

1. 1
   ДругоеThe volatiles were removed in vacuo
2. 2
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
3. 3
   workup.ADDITIONtreated with saturated aqueous NH4Cl
4. 4
   СушкаThe organic layer was dried over MgSO4
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated in vacuo
7. 7
   ДругоеPurification by chromatography on silica gel (100 g, 30% ethyl acetate: hexanes)

Методика

To a solution of 4-methoxy-4-[3-(tetrahydropyran-2-yloxy)-prop-1-ynyl]tetrahydropyran (3.8 g, 14.8 mmol), prepared as in step 2, in methanol (50 mL), was added a catalytic amount of pyridinium p-toluenesulfonate (PPTS). The resulting yellow solution was stirred under nitrogen for 17 hours at ambient temperature. The volatiles were removed in vacuo and the residue was dissolved in ethyl acetate and treated with saturated aqueous NH4Cl. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. Purification by chromatography on silica gel (100 g, 30% ethyl acetate: hexanes) provided 4-methoxy-4-(3-hydroxyprop-1-ynyl)tetrahydropyran (1.2 g, 47 %) as a colorless oil.

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