反応 #67524

反応方程式

3,4-Dihydro-2H-pyran

1

4-Bromo-1-butanol

→

product 2

収率 92.3%

2-(4-Bromobutoxy)-tetrahydro-2H-pyran

収率 92.3%

溶媒

dichloromethane

反応条件

後処理

1. 1
   その他After removing the solvent
2. 2
   その他the residue was purified by flash chromatography on silica gel with 5:1 hexanes/ethyl acetate as the eluent

実験手順

3,4-Dihydro-2H-pyran (8.5 mL, 90.96 mmol) was added dropwise to the dichloromethane (20 mL) solution of 1 (10.7 g, 69.93 mmol) and p-toluenesulfonic acid monohydrate (26.5 mg, 0.1372 mmol). The mixture was stirred at room temperature over night. After removing the solvent, the residue was purified by flash chromatography on silica gel with 5:1 hexanes/ethyl acetate as the eluent to yield product 2 as a colorless oil (15.3 g, 92%). 1H NMR (400 MHz, CDCl3): δ 1.48-1.62 (m, 4H), 1.68-1.85 (m, 4H), 1.94-2.02 (m, 2H), 3.40-3.53 (m, 4H), 3.74-3.88 (m, 2H), 4.57-4.59 (m, 1H).

出典