Reaktion #1193751

Reaktionsgleichung

7-hydroxy-1-tetralone

caesium carbonate

benzylbromide

→

7-Benzyloxy-3,4-dihydro-1(2H)naphthalenone

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe mixture then filtered
2. 2
   Einengenthe filtrate concentrated in vacuo
3. 3
   SonstigeThe oily residue was partitioned between ethyl acetate (200 ml) and brine (200 ml)
4. 4
   Sonstigethe organic layer separated
5. 5
   Trocknendried (MgSO4)
6. 6
   Einengenconcentrated in vacuo

Vorschrift

7-Benzyloxy-3,4-dihydro-1(2H)naphthalenone was prepared by treating 7-hydroxy-1-tetralone (5.91 g, 36.4 mmol) and caesium carbonate (13 g, 40.0 mmol) in dry DMF (100 ml) and under N2 with benzylbromide (6.22 g, 4.33 ml, 36.4 mmol). The reaction was stirred for 3 h and the mixture then filtered and the filtrate concentrated in vacuo. The oily residue was partitioned between ethyl acetate (200 ml) and brine (200 ml), the organic layer separated, dried (MgSO4) and concentrated in vacuo. Trituration of the resultant solid with diethylether-hexane (1:1, 200 ml) gave the desired compound as a white solid (6.57 g) m.p. 86-87°. MS (EI, 60 V) 252 (M+, 100%).

Quelle