Dimethylformamide → Methyl 3-formyl-4,5-dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]pyrrole-2-carboxylate

HRID 433882ノート

反応式

HRID 433882 の反応式
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[CH3:11][C:12]1[CH:13]=[C:14]([C:23]([O:25][CH3:26])=[O:24])[N:15]([CH2:18][C@H:19]2[CH2:21][C@@H:20]2[CH3:22])[C:16]=1[CH3:17].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.O>[CH:8]([C:13]1[C:12]([CH3:11])=[C:16]([CH3:17])[N:15]([CH2:18][C@H:19]2[CH2:21][C@@H:20]2[CH3:22])[C:14]=1[C:23]([O:25][CH3:26])=[O:24])=[O:9]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 69367093methyl 4,5-dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]pyrrole-2-carboxylate

生成物 1

HCID 12110455Methyl 3-formyl-4,5-dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]pyrrole-2-carboxylate収率 78.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒2 回

実験手順

Phosphorous oxychloride (2.15 g, 14 mmol) was added to a solution of dimethylformamide (1.10 g, 15 mmol) in toluene (2 ml) and the mixture was stirred at room temperature for 30 minutes. To this mixture was added a solution of methyl 4,5-dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]pyrrole-2-carboxylate (2.21 g, 10 mmol) in toluene (6 ml) and the mixture was then heated at 80° C. for 10 hours. After this time, the reaction mixture was poured into water and neutralized with saturated aqueous sodium hydrogencarbonate solution. The organic layer was separated and was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and then concentrated in vacuo. The residue was chromatographed on a column using ethyl acetate/hexane=10/1 as the eluant to afford the title compound (1.95 g, 78.2%) as a pale yellow oil.

後処理

  1. temperaturethe mixture was then heated at 80° C. for 10 hours
  2. customThe organic layer was separated
  3. washwas washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on a column

出典と根拠

ORDレコード
ord-2e27a79cd5c34244975ff0931fdf9aec
出典データセット
uspto-grants-2003_12
特許番号
US06670360B2

反応ノート

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