تفاعل #50177

معادلة التفاعل

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

المردود 96.1%

المذيبات

THF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر