Reaktion #1256497

Reaktionsgleichung

3-hydroxy-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene

potassium carbonate

benzyl bromide

→

3-benzyloxy-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene

Ausbeute 104.8%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated under reduced pressure
2. 2
   workup.ADDITIONthe residue was mixed with water (20 ml)
3. 3
   Extraktionextracted with ethyl acetate (20 ml×3)
4. 4
   TrocknenThe combined organic layers were dried with anhydrous magnesium sulfate
5. 5
   Einengenwere then concentrated under reduced pressure
6. 6
   EinengenThe objective fractions were concentrated under reduced pressure

Vorschrift

To 3-hydroxy-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene (1.76 g, 10.0 mmol) dissolved in DMF (10 ml) were added potassium carbonate (2.76 g, 20.2 mmol) and benzyl bromide (1.308 ml, 11.0 mmol), and the resulting mixture was stirred at room temperature for 24 hours. The reaction mixture was concentrated under reduced pressure, and the residue was mixed with water (20 ml) and extracted with ethyl acetate (20 ml×3). The combined organic layers were dried with anhydrous magnesium sulfate and were then concentrated under reduced pressure, and the residue was subjected to column chromatography (silica gel: 35 g, ethyl acetate/hexane=1/9). The objective fractions were concentrated under reduced pressure to obtain 3-benzyloxy-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene (2.79 g).

Quelle