反応 #2487405

反応方程式

3-Cyclohexene-1-methanol

NaH

MeI

→

4-(Methoxymethyl)cyclohexene

溶媒

THF

THF

THF

water

反応条件

後処理

1. 1
   抽出was extracted with diethyl ether (2×30 mL)
2. 2
   乾燥The organic layer was dried over Na2SO4
3. 3
   濃縮was concentrated by rotory evaporation
4. 4
   workup.DISTILLATIONwas distilled
5. 5
   その他time=1.59 min, m/z calcd

実験手順

3-Cyclohexene-1-methanol (8.92 mmol, 1.00 g) and NaH (17.8 mmol, 428 mg) were mixed in THF (30 mL) at rt, and the THF solution was stirred for 1 h at rt. MeI (17.8 mmol, 1.10 mL) was added slowly into the above THF solution. After stirring for 16 h at rt, the solution was diluted with water (30 ml), and then was extracted with diethyl ether (2×30 mL). The organic layer was dried over Na2SO4, was concentrated by rotory evaporation, and then was distilled to generate the final product 17 as a colorless liquid (460 mg, 41%). 1H-NMR (500 MHz) δ 5.68 (m, 2H), 3.36 (s, 3H), 3.28 (dd, J=6.5 Hz, J=4 Hz), 2.06-2.14 (m, 3H), 1.92 (m, 1H), 1.83 (m, 1H), 1.75 (m, 1H), 1.29 (m, 1H). 13C-NMR (100 MHz) δ 127.2, 126.1, 78.0, 58.9, 34.0, 28.6, 25.8, 24.7. LC-MS (APCI): Peak time=1.59 min, m/z calcd for C8H15O [M+H]+ 127.11, found 127.10.

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