반응 #746796

반응 방정식

N,N-dimethylformamide

POCl3

9-benzyl-9H-carbazole

→

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

수율 36.3%

용매

EtOAc

반응 조건

후처리

1. 1
   workup.STIRRINGto stir at room temperature for 1 hour
2. 2
   온도Then, the temperature was raised to 95° C. in an oil bath
3. 3
   workup.STIRRINGto stir for 18 hours
4. 4
   온도Upon completion, the reaction mixture was cooled down to room temperature
5. 5
   기타quenched with water (20 mL)
6. 6
   workup.STIRRINGto stir for an additional 4 hours at room temperature
7. 7
   여과The solids were collected by filtration
8. 8
   기타dried

실험 절차

A 50-mL 3-necked round-bottomed flask was charged with N,N-dimethylformamide (400 mg, 5.42 mmol, 2.80 equiv, 99%). To this, POCl3 (700 mg, 4.56 mmol, 2.40 equiv, 99%) was added drop wise with stirring at 0° C. and allowed to stir at room temperature for 1 hour. To this mixture was added 9-benzyl-9H-carbazole (500 mg, 1.93 mmol, 1.00 equiv, 99%) in small portions at 45° C. over 5 minutes. Then, the temperature was raised to 95° C. in an oil bath and allowed to stir for 18 hours. The progress was monitored by TLC (EtOAc:PE=1:4). Upon completion, the reaction mixture was cooled down to room temperature and quenched with water (20 mL). The resulting mixture was allowed to stir for an additional 4 hours at room temperature. The solids were collected by filtration and dried to afford 9-benzyl-9H-carbazole-3-carbaldehyde as green solid (200 mg, 36.1%). LCMS: [M+H]+: 286

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