반응 #50177

반응 방정식

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

수율 96.1%

용매

THF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   기타The reaction was quenched by addition of crushed ice and saturated aqueous NH4Cl
3. 3
   추출The resulting two-phase mixture was extracted with ether (3×100 mL)
4. 4
   건조The combined organic layers were dried over MgSO4
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo
7. 7
   기타Purification by chromatography on silica gel (100 g, 10% ethyl acetate: hexanes)

실험 절차

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.

출처