Reaktion #44000

Reaktionsgleichung

sodium hydroxide

3-Hydroxy-4-methoxynaphtho[2,3-c]furan-1(3H)-one

ethyl 4-aminophenylacetate

Sodium triacetoxyborohydride

→

ethyl[4-(4-methoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate

Ausbeute 54.5%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with dichloromethane (3×5 ml)
2. 2
   SonstigeThe combined extracts were evaporated under vacuum
3. 3
   Sonstigethe residue triturated with cyclohexane/ether

Vorschrift

3-Hydroxy-4-methoxynaphtho[2,3-c]furan-1(3H)-one (50 mg, 0.22 mmol) and ethyl 4-aminophenylacetate (47 mg, 0.26 mmol) in dichloromethane (5 ml) were stirred at room temperature under nitrogen for 1 hour. Sodium triacetoxyborohydride (138 mg, 0.66 mmol) was added and stirring continued for 24 h. The reaction was adjusted to pH14 with sodium hydroxide solution (2N) and extracted with dichloromethane (3×5 ml). The combined extracts were evaporated under vacuum and the residue triturated with cyclohexane/ether to give ethyl[4-(4-methoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate as a white solid (45 mg, 54%).

Quelle