5-Iodo-N,N-dimethyl-2-nitrobenzamide → 3-(3-Dimethylcarbamoyl-4-nitrophenyl)propionic acid ethyl ester

HRID 423269

反応式

HRID 423269 の反応式
I[C:2]1[CH:3]=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([CH:12]=1)[C:7]([N:9]([CH3:11])[CH3:10])=[O:8].[Br-].[CH2:17]([O:19][C:20](=[O:24])[CH2:21][CH2:22][Zn+])[CH3:18]>O1CCCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:17]([O:19][C:20](=[O:24])[CH2:21][CH2:22][C:2]1[CH:3]=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([C:7](=[O:8])[N:9]([CH3:11])[CH3:10])[CH:12]=1)[CH3:18]

参加物

5

反応物 2

HCID 666767645-Iodo-N,N-dimethyl-2-nitrobenzamideHCID 178471816HCID 178471816、化合物

生成物 1

HCID 666758683-(3-Dimethylcarbamoyl-4-nitrophenyl)propionic acid ethyl ester

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

5-Iodo-N,N-dimethyl-2-nitrobenzamide (2.00 g) was dissolved in tetrahydrofuran (20 mL) and bis(triphenylphosphine)palladium(II) dichloride (0.128 g) was added thereto. After cooling down to 0° C., 0.5M 3-ethoxy-3-oxopropylzinc bromide solution (22.5 mL) was added dropwise thereto, the mixture was stirred at room temperature overnight. The reaction solution was concentrated, dissolved in ethyl acetate (100 mL), washed successively with 1N hydrochloric acid (30 mL) and saturated brine (30 mL), and dried over sodium sulfate. Further, the mixture was purified by column chromatography on silica gel (ethyl acetate:hexane=3:2, v/v) to give the title compound (1.52 g) as a brown oil.

後処理

  1. concentrationThe reaction solution was concentrated
  2. dissolutiondissolved in ethyl acetate (100 mL)
  3. washwashed successively with 1N hydrochloric acid (30 mL) and saturated brine (30 mL)
  4. dry with materialdried over sodium sulfate
  5. customFurther, the mixture was purified by column chromatography on silica gel (ethyl acetate

出典と根拠

ORDレコード
ord-9687531aeefc4263b81c83d83d3846b5
出典データセット
uspto-grants-2012_01
特許番号
US08101774B2

関連ノート

読み込み中…