反応 #50178

反応方程式

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

pyridinium p-toluenesulfonate

→

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

収率 47.6%

溶媒

methanol

反応条件

後処理

1. 1
   その他The 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
   乾燥The organic layer was dried over MgSO4
5. 5
   ろ過filtered
6. 6
   濃縮concentrated in vacuo
7. 7
   その他Purification by chromatography on silica gel (100 g, 30% ethyl acetate: hexanes)

実験手順

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.

出典