Reaktion #79605

Reaktionsgleichung

5-carbomethoxy-1,2-dihydro-2-methyl-9H-carbazol-4(3H)-one

3-methylbenzyl bromide

potassium carbonate

→

9-[(3-methylphenyl)methyl]-5-carbomethoxy-2-methyl-1,2-dihydrocarbazol-4(3H)-one

Ausbeute 100.0%

Lösungsmittel

EtOAc

HCl

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe layers were separated
2. 2
   Extraktionthe aqueous layer extracted with EtOAc
3. 3
   ExtraktionThe combined EtOAc layers were extracted with 1N HCl, water
4. 4
   SonstigeAfter drying
5. 5
   Sonstige(NaSO4), evaporation in vacuo

Vorschrift

A suspension of 5-carbomethoxy-1,2-dihydro-2-methyl-9H-carbazol-4(3H)-one (1.0 g, 3.89 mM), 3-methylbenzyl bromide (0.54 ml, 3.97 mM), and potassium carbonate (1.07 g, 7.78 mM) in 20 mL DMF was stirred at room temperature for 19 hours. The mixture was diluted with EtOAc and 1N HCl. The layers were separated and the aqueous layer extracted with EtOAc. The combined EtOAc layers were extracted with 1N HCl, water, then brine. After drying (NaSO4), evaporation in vacuo afforded 1.41 g (100%) of 9-[(3-methylphenyl)methyl]-5-carbomethoxy-2-methyl-1,2-dihydrocarbazol-4(3H)-one. 1H NMR (CDCl3) δ7.4-7.05 (m, 6H), 6.8 (m, 1H), 5.3 (s, 2H), 4.05 (s, 3H), 3.0 (m, 1H), 2.7-2.3 (m, 4H), 2.3 (s, 1H), 1.2 (d, J=7 Hz, 3H). MS (ES) m/e 362.

Quelle