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Dimethylformamide → 9-Benzyl-3-formylcarbazole

HRID 659614
ノート
印刷プレビュー

反応式

HRID 659614 の反応式
CN(C)[CH:3]=[O:4].O=P(Cl)(Cl)Cl.[CH2:11]([N:18]1[C:30]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CCOC(C)=O>[CH2:11]([N:18]1[C:19]2[CH:20]=[CH:21][C:22]([CH:3]=[O:4])=[CH:23][C:24]=2[C:25]2[C:30]1=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 146485N-Benzylcarbazole

生成物 1

HCID 30915349-Benzyl-3-formylcarbazole収率 36.3%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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

後処理

  1. stirringto stir at room temperature for 1 hour
  2. temperatureThen, the temperature was raised to 95° C. in an oil bath
  3. stirringto stir for 18 hours
  4. temperatureUpon completion, the reaction mixture was cooled down to room temperature
  5. customquenched with water (20 mL)
  6. stirringto stir for an additional 4 hours at room temperature
  7. filtrationThe solids were collected by filtration
  8. customdried

出典と根拠

ORDレコード
ord-51d5def88816466c93d27c67a79c1724
出典データセット
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08080566B1

反応ノート

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