Reaktion #3454

Reaktionsgleichung

4-Methoxy-2-methyl-1H-indole

NaH

1-(chloromethyl)naphthalene

→

4-methoxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole

Ausbeute 97.1%

Lösungsmittel

DMF

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITAfter 5 hours
2. 2
   Extraktionextracted twice with ethyl acetate
3. 3
   WaschenThe combined ethyl acetate was washed with brine
4. 4
   Trocknendried (MgSO4)
5. 5
   Einengenconcentrated at reduced pressure
6. 6
   SonstigeThe residue was chromatographed on silica gel
7. 7
   Wascheneluted with 20% EtOAc/hexane

Vorschrift

4-Methoxy-2-methyl-1H-indole (644 mg, 4 mmol) was dissolved in 10 mL of DMF and 160 mg (4 mmol) of 60% NaH/mineral oil was added. After 0.67 hours, 707 mg (4 mmol) of 1-(chloromethyl)naphthalene was added. After 5 hours, the mixture was diluted with water and extracted twice with ethyl acetate. The combined ethyl acetate was washed with brine, dried (MgSO4) and concentrated at reduced pressure. The residue was chromatographed on silica gel and eluted with 20% EtOAc/hexane to give 1.17 g (97% yield) of 4-methoxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole.

Quelle