반응 #746797

반응 방정식

AlCl3

9-benzyl-9H-carbazole-3-carbaldehyde

→

9H-carbazole-3-carbaldehyde

수율 40.0%

용매

1,2-dichloroethane

반응 조건

후처리

1. 1
   기타The reaction was then quenched by the addition of H2O/ice (100 mL)
2. 2
   여과The solids were filtered out
3. 3
   추출The resulting solution was extracted with DCM (3×100 mL)
4. 4
   농축the combined organic layers were concentrated on a rotary evaporator
5. 5
   기타to give a residue that
6. 6
   기타was purified by silica gel column chromatography
7. 7
   세척eluted with PE

실험 절차

A 250-mL round-bottomed flask was charged with a solution of AlCl3 (9.26 g, 69.45 mmol, 20.00 equiv, 99%) in 1,2-dichloroethane (150 mL). To this was added 9-benzyl-9H-carbazole-3-carbaldehyde (1 g, 3.47 mmol, 1.00 equiv, 99%) in several batches at room temperature over 5 minutes. The resulting mixture was stirred for 2 hours at room temperature. The reaction was then quenched by the addition of H2O/ice (100 mL). The solids were filtered out. The resulting solution was extracted with DCM (3×100 mL) and the combined organic layers were concentrated on a rotary evaporator to give a residue that was purified by silica gel column chromatography eluted with PE:EtOAc (10:1) to afford 9H-carbazole-3-carbaldehyde as green solid (270 mg, 40%). LCMS: [M+H]+: 196

출처