Reaktion #91363

Reaktionsgleichung

6-hydroxy-3,4-dihydro-1(2H)-naphthalenone

(2-bromoethyl)benzene

potassium carbonate

→

title compound

Ausbeute 61.1%

6-(2-phenylethoxy)-1,2,3,4-tetrahydronaphthalen-1-one

Ausbeute 61.1%

Lösungsmittel

ACN

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe solution was heated
2. 2
   Temperaturat reflux overnight
3. 3
   FiltrationThe reaction was filtered
4. 4
   Einengenconcentrated
5. 5
   Sonstigepurified by silica gel chromatography (PE/EtOAc/DCM=10:1:2)

Vorschrift

To a solution of 6-hydroxy-3,4-dihydro-1(2H)-naphthalenone (2.0 g, 12.3 mmol) and (2-bromoethyl)benzene (4.8 g, 25.8 mmol) in ACN (20 mL) was added potassium carbonate (3.4 g, 24.6 mmol) at rt. The solution was heated at reflux overnight. The reaction was filtered, concentrated, and purified by silica gel chromatography (PE/EtOAc/DCM=10:1:2) to give 2.0 g (61%) of the title compound as a brown oil. 1H NMR (300 MHz, CDCl3): δ 2.08-2.16 (2H, m), 2.62 (2H, t, J=6.3 Hz), 2.92 (2H, t, J=6.3 Hz), 3.13 (2H, t, J=7.2 Hz), 2.92 (2H, t, J=7.2 Hz), 6.71 (1H, d, J=2.1 Hz), 6.83 (1H, dd, J=2.4, 8.7 Hz), 7.27-7.38 (5H, m), 8.01 (1H, dd, J=8.7 Hz).

Quelle