Dimethylformamide → 5-Methyl-3-(propan-2-yl)-1H-pyrrole-2-carbaldehyde

HRID 1828894ノート

反応式

HRID 1828894 の反応式
CN([CH:4]=[O:5])C.O=P(Cl)(Cl)Cl.[CH:11]([C:14]1[CH:18]=[C:17]([CH3:19])[NH:16][CH:15]=1)([CH3:13])[CH3:12].[OH-].[Na+]>ClC(Cl)C.O>[CH:11]([C:14]1[CH:18]=[C:17]([CH3:19])[NH:16][C:15]=1[CH:4]=[O:5])([CH3:13])[CH3:12]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 22059886HCID 22059886、化合物

生成物 1

HCID 220592415-Methyl-3-(propan-2-yl)-1H-pyrrole-2-carbaldehyde収率 67%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 63651,1-Dichloroethane溶媒2 回

実験手順

To a solution of anhydrous DMF (2.1 ml, 27 mmol) in anhydrous dichloroethane (50 ml) at 0° C. under nitrogen, POCl3 (2.1 ml, 23 mmol) was added dropwise. The solution was allowed to warm at room temperature for 1 h. Then, the suspension was cooled at 0° C. and a solution of 3-isopropyl-5-methylpyrrole (2 g, 16 mmol) in dichloroethane (20 ml) was added dropwise over 20 min. After stirring at room temperature for 24 h, water followed by NaOH were added to pH: 8. The organic layer was extracted, dried and the solvent removed to dryness. The residue was purified by flash chromatography. Yield 67%, m.p. 90–93° C.

後処理

  1. temperatureThen, the suspension was cooled at 0° C.
  2. additionwere added to pH: 8
  3. extractionThe organic layer was extracted
  4. customdried
  5. customthe solvent removed to dryness
  6. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-616fe5dc6f4b45529faa580385fed4d3
出典データセット
uspto-grants-2006_06
特許番号
US07060822B1

反応ノート

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