反应 #50177

反应方程式

hydrogen

sodium hydride

methyl iodide

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

→

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

收率 96.1%

溶剂

THF

反应条件

后处理

1. 1
   workup.ADDITIONwas added
2. 2
   其他The reaction was quenched by addition of crushed ice and saturated aqueous NH4Cl
3. 3
   萃取The resulting two-phase mixture was extracted with ether (3×100 mL)
4. 4
   干燥The combined organic layers were dried over MgSO4
5. 5
   过滤filtered
6. 6
   浓缩concentrated in vacuo
7. 7
   其他Purification by chromatography on silica gel (100 g, 10% ethyl acetate: hexanes)

实验过程

To a suspension of sodium hydride (1.2 g of an 80% oil dispersion, 50 mmol) in dry THF (45 mL) was added a solution of 4-hydroxy-4-[3-(tetrahydropyran-2-yloxy)-prop-1-ynyl]tetrahydropyran(3.71 g, 15.3 mmol), prepared as in step 1. After hydrogen evolution ceased, methyl iodide (3.0 mL, 48.2 mmol) was added neat and the resulting solution was stirred overnight at ambient temperature. The reaction was quenched by addition of crushed ice and saturated aqueous NH4Cl. The resulting two-phase mixture was extracted with ether (3×100 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. Purification by chromatography on silica gel (100 g, 10% ethyl acetate: hexanes) provided 4-methoxy-4-[3-(tetrahydropyran-2-yloxy)prop-1-ynyl]tetrahydropyran (3.74 g, 95 %) as a colorless oil.

来源