反応 #639628

反応方程式

water

4-bromo-3-(hydroxymethyl)-2-propylphenol

p-toluenesulfonic acid-hydrate

3,4-dihydro-2H-pyrane

→

title compound

収率 70.0%

4-bromo-2-propyl-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]phenol

収率 70.0%

溶媒

dichloromethane

反応条件

後処理

1. 1
   抽出extracted with chloroform
2. 2
   洗浄Subsequently, the organic layer was washed with saturated saline
3. 3
   その他dried
4. 4
   濃縮concentrated in vacuum
5. 5
   その他The residue was purified by silica-gel column chromatography (hexane/ethyl acetate)

実験手順

To a solution of 4-bromo-3-(hydroxymethyl)-2-propylphenol (1.04 g, 4.24 mmol) in dichloromethane (50 mL), p-toluenesulfonic acid-hydrate (81 mg, 0.424 mmol) and 3,4-dihydro-2H-pyrane (535 mg, 6.36 mmol) were added at room temperature. The mixture was stirred at same temperature for 5 hours. The reaction solution was added with water and extracted with chloroform. Subsequently, the organic layer was washed with saturated saline, dried using anhydrous sodium sulfate, and concentrated in vacuum. The residue was purified by silica-gel column chromatography (hexane/ethyl acetate) and the title compound (972 mg, 70%) was obtained as colorless oil.

出典