反応 #50177

反応方程式

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

収率 96.1%

溶媒

THF

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   その他The reaction was quenched by addition of crushed ice and saturated aqueous NH4Cl
3. 3
   抽出The resulting two-phase mixture was extracted with ether (3×100 mL)
4. 4
   乾燥The combined organic layers were 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, 10% ethyl acetate: hexanes)

実験手順

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.

出典