Dimethylformamide → 5-Dodecylthiophene-2-carbaldehyde

HRID 892386

反応式

HRID 892386 の反応式
CN(C)[CH:3]=[O:4].O=P(Cl)(Cl)Cl.[CH2:11]([C:23]1[S:24][CH:25]=[CH:26][CH:27]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>O>[CH2:11]([C:23]1[S:24][C:25]([CH:3]=[O:4])=[CH:26][CH:27]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 5663472-Dodecylthiophene

生成物 1

HCID 149850895-Dodecylthiophene-2-carbaldehyde収率 75.9%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
5 °C

実験手順

In a 1 liter-four-necked flask, 93.7 g (1.28 mol) of N,N-dimethylformamide was placed and cooled to 5° C., followed by addition of 107.4 g (7.00×10-1 mol) of POCl3 in 15 min. below 10° C. under stirring. After stirring for 30 min. below 10° C., 160 g (6.35×10-1 mol) of 2-dodecylthiophene was added dropwise to the mixture in 10 min. at room temperature, followed by stirring for 1.5 hours and further stirring for 2.5 hours at 60° C. After the reaction, the reaction mixture was poured into 2 liter of iced water, subjected to 3 times of extraction with 500 ml of chloroform and washed 6 times with 500 ml of water. The organic layer was dried on CaCl2, followed by distilling-off of the solvent to obtain 237 g of a crude product. The crude product was subjected to reduced-pressure distillation in an atmosphere of nitrogen to obtain 135 g of a product (yield: 75.9%). b.p.: 160° C./0.6 mmHg

後処理

  1. stirringAfter stirring for 30 min. below 10° C.
  2. stirringby stirring for 1.5 hours
  3. stirringfurther stirring for 2.5 hours at 60° C
  4. customAfter the reaction
  5. extractionsubjected to 3 times of extraction with 500 ml of chloroform
  6. washwashed 6 times with 500 ml of water
  7. customThe organic layer was dried on CaCl2
  8. customto obtain 237 g of a crude product
  9. distillationThe crude product was subjected to reduced-pressure distillation in an atmosphere of nitrogen

出典と根拠

ORDレコード
ord-559be8ca61c24572ade9750d3c439cd1
出典データセット
uspto-grants-1992_06
特許番号
US05118441

関連ノート

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