Reaktion #639628

Reaktionsgleichung

water

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

p-toluenesulfonic acid-hydrate

3,4-dihydro-2H-pyrane

→

title compound

Ausbeute 70.0%

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

Ausbeute 70.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with chloroform
2. 2
   WaschenSubsequently, the organic layer was washed with saturated saline
3. 3
   Sonstigedried
4. 4
   Einengenconcentrated in vacuum
5. 5
   SonstigeThe residue was purified by silica-gel column chromatography (hexane/ethyl acetate)

Vorschrift

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.

Quelle