Hydrochloric Acid → Benzyl 4-[3-(3-nitrobenzyl)indol-1-yl]-4-oxobutyrate

HRID 249155ノート

反応式

HRID 249155 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].[C:22]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)(=[O:34])[CH2:23][CH2:24][C:25](OC1C=CC=CC=1)=[O:26].Cl>CN(C)C=O.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:25](=[O:26])[CH2:24][CH2:23][C:22]([O:35][CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[O:34])[CH:9]=1)([O-:3])=[O:2]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 190247043-(3-Nitrobenzyl)indoleHCID 19024784Benzyl phenyl succinate

生成物 1

HCID 19024729Benzyl 4-[3-(3-nitrobenzyl)indol-1-yl]-4-oxobutyrate収率 74.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒3 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
25 °C

実験手順

A solution of 3-(3-nitrobenzyl)indole (280 mg) in N,N-dimethylformamide (5 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 66.6 mg) in N,N-dimethylformamide (10 ml) at 0° C. The mixture was stirred at 25° C. for 40 minutes, and a solution of benzyl phenyl succinate (316 mg) in N,N-dimethylformamide was added at -40° C. After stirred at -40° C. for 20 minutes, the reaction mixture was poured into a mixture of ethyl acetate and 1N hydrochloric acid. The organic layer was separated, washed with water and brine, and dried over, magnesium sulfate. After evaporation of the solvent, the crude crystals were washed with hot isopropyl ether to give benzyl 4-[3-(3-nitrobenzyl)indol-1-yl]-4-oxobutyrate (364 mg).

後処理

  1. stirringAfter stirred at -40° C. for 20 minutes
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over, magnesium sulfate
  5. customAfter evaporation of the solvent
  6. washthe crude crystals were washed with hot isopropyl ether

出典と根拠

ORDレコード
ord-f987f97db3f54769b1057ea5e79dfa11
出典データセット
uspto-grants-1993_05
特許番号
US05212320

反応ノート

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