反応 #978421

反応方程式

hexaethylene glycol monobenzyl ether

NaH

triethylene glycol methyl tosyl ether

→

nonaethylene glycol benzyl methyl ether

収率 88.0%

溶媒

THF

THF

THF

反応条件

後処理

1. 1
   温度The mixture was refluxed under nitrogen overnight
2. 2
   温度cooled to ambient temperature
3. 3
   その他quenched with water (500 ml)
4. 4
   抽出extracted with diethyl ether (3×300 ml)
5. 5
   乾燥dried (sodium sulfate)
6. 6
   濃縮concentrated in vacuo

実験手順

A solution of hexaethylene glycol monobenzyl ether from above (22.3 g) in anhydrous THF (100 ml) was added to a suspension of 50% NaH (3.5 g) in anhydrous THF (100 ml). The suspension was stirred at ambient temperature for 30 min and then a solution of triethylene glycol methyl tosyl ether from above (22.0 g) in THF (100 ml) was added dropwise. The mixture was refluxed under nitrogen overnight, cooled to ambient temperature, quenched with water (500 ml), and extracted with diethyl ether (3×300 ml). The ether extracts were combined, dried (sodium sulfate), and concentrated in vacuo to give nonaethylene glycol benzyl methyl ether as an oil (27 g, 88%), 1H-NMR (CDCl3) δ: 7.31 (m, 5, 5 phenyl CH), 4.54 (s, 2, benzyl CH2), 3.62–3.52 (m, 36, 18 CH2O), 3.35 (s, 3, CH3).

出典