Benzyl chloroformate → 1-Benzyloxycarbonyl-5-chloro-3-formylindol

HRID 564846

반응식

HRID 564846 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]=[O:12].[H-].[Na+].[C:15](Cl)([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]>O1CCCC1>[CH2:18]([O:17][C:15]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[C:5]([CH:11]=[O:12])=[CH:6]1)=[O:16])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

5

반응물 3

HCID 10387Benzyl chloroformateHCID 24758Sodium hydrideHCID 27953745-chloro-1H-indole-3-carbaldehyde

생성물 1

HCID 184739871-Benzyloxycarbonyl-5-chloro-3-formylindol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 5-chloro-3-formylindole (5.00 g) in tetrahydrofuran (135 ml) was added sodium hydride (60% oil suspension, 3.53 g). The mixture was stirred for 20 minutes at room temperature. Carbobenzoxychloride (6.64 ml) was added to the mixture. After being stirred for 1 hour at room temperature, the whole was poured into ice water. The mixture was extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. The solution was concentrated to give a residue, which was subjected to silica gel chromatography. Elution with hexane-ethyl acetate (5:1) provided 1-benzyloxycarbonyl-5-chloro-3-formylindol (5.74 g) as a crystal.

후처리

  1. stirringAfter being stirred for 1 hour at room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe solution was concentrated
  6. customto give a residue, which
  7. washElution with hexane-ethyl acetate (5:1)

출처 및 근거

ORD 기록
ord-634f65947fe743918acd6f1641032b35
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06169102A

연결된 노트

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