Dimethylformamide → ethyl 4-chloro-3-formyl-5-methyl-1H-pyrrole-2-carboxylate

HRID 1948346ノート

反応式

HRID 1948346 の反応式
O=P(Cl)(Cl)Cl.CN([CH:9]=[O:10])C.[Cl:11][C:12]1[CH:13]=[C:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[NH:15][C:16]=1[CH3:17].C([O-])(=O)C.[Na+]>ClCCCl.O>[Cl:11][C:12]1[C:13]([CH:9]=[O:10])=[C:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[NH:15][C:16]=1[CH3:17]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 66707189ethyl 4-chloro-5-methyl-1H-pyrrole-2-carboxylate

生成物 1

HCID 86643343ethyl 4-chloro-3-formyl-5-methyl-1H-pyrrole-2-carboxylate収率 30.7%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒2 回HCID 962Water溶媒

実験手順

POCl3 in 1,2-dichloroethane (14 mL) was slowly added to a solution of DMF (4.37 mL, 59.79 mmol) in 1,2-dichloroethane (10 mL). The reaction mixture was stirred for 15 min and then Intermediate 7 (2.04 g, 10.87 mmol) was added. The reaction mixture was heated at reflux for 3 h and then cooled to room temperature. The reaction mixture was treated with sodium acetate (10 g) in water (25 mL) and stirred for 1 h. The mixture was extracted with methylene chloride, washed with water, dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 2:1 hexanes/ethyl acetate) gave the desired compound (720 mg).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 h
  3. stirringstirred for 1 h
  4. extractionThe mixture was extracted with methylene chloride
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customPurification by flash column chromatography (silica, 2:1 hexanes/ethyl acetate)

出典と根拠

ORDレコード
ord-241e38d15191409aaa061f430f68e776
出典データセット
uspto-grants-2013_03
特許番号
US08399489B2

反応ノート

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