Pyrrole-2-carboxaldehyde → 1-[2-Nitro-5-(ethoxycarbonyl)benzyl]-pyrrole-2-carboxaldehyde

HRID 3602

反応式

HRID 3602 の反応式
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH:8]=[O:9].[N+:10]([C:13]1[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][C:14]=1[CH2:24]Br)([O-:12])=[O:11]>O1CCCC1>[N+:10]([C:13]1[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][C:14]=1[CH2:24][N:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH:8]=[O:9])([O-:12])=[O:11]

参加物

5

反応物 3

HCID 13854Pyrrole-2-carboxaldehydeHCID 24758Sodium hydrideHCID 130774453-Bromomethyl-4-nitro-benzoic acid ethyl ester

生成物 1

HCID 218371151-[2-Nitro-5-(ethoxycarbonyl)benzyl]-pyrrole-2-carboxaldehyde収率 83.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
20 °C

実験手順

To a stirred slurry of 2.2 g of sodium hydride (60% in oil, washed with hexane) in tetrahydrofuran is added at 0° C. a solution of 4.5 g of pyrrole-2-carboxaldehyde in 25 ml of tetrahydrofuran. After the addition is complete, a solution of 15 g of ethyl 4-nitro-3-bromomethylbenzoate in 30 ml of dry tetrahydrofuran is slowly added under nitrogen. The reaction mixture is stirred at 20° C. for 8 hours and carefully quenched with water. The reaction mixture is extracted with chloroform which is washed with water, dried with Na2SO4 and concentrated in vacuo to give 12 g of the desired product as a solid; mass spectrum (M+ H)349.

後処理

  1. additionAfter the addition
  2. customcarefully quenched with water
  3. extractionThe reaction mixture is extracted with chloroform which
  4. washis washed with water
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-169b2f504f264086a66d2edfe51fb873
出典データセット
uspto-grants-1998_03
特許番号
US05733905

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