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

HRID 249155노트

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HRID 249155 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매3회HCID 8857Ethyl Acetate용매

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온도
25 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f987f97db3f54769b1057ea5e79dfa11
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05212320

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