Hydrochloric Acid → 2a-(4-Pentenyl)-2a,3,4,5-tetrahydrobenzo[cd]indol-2(1H)-one

HRID 2301132노트

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HRID 2301132 반응식
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[CH2:10][CH2:11][CH2:12][CH:3]([C:4]=23)[C:2]1=[O:13].[H-].[Na+].Br[CH:17]=[CH:18][CH2:19][CH2:20][CH3:21].Cl>CN(C)C=O.O.C(OCC)(=O)C>[CH2:21]([C:3]12[CH2:12][CH2:11][CH2:10][C:5]3[C:4]1=[C:9]([CH:8]=[CH:7][CH:6]=3)[NH:1][C:2]2=[O:13])[CH2:20][CH2:19][CH:18]=[CH2:17]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 5993752a,3,4,5-Tetrahydrobenzo[cd]indol-2(1H)-oneHCID 544479931-Bromo-1-pentene

생성물 1

HCID 3732662a-(4-Pentenyl)-2a,3,4,5-tetrahydrobenzo[cd]indol-2(1H)-one

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

2a,3,4,5-Tetrahydro-1H-benz[cd]indol-2-one (4.0 g, 23 mmol) was dissolved in anhydrous N,N-dimethylformamide (100 ml), and the solution was mixed with sodium hydride (760 mg, 190 mmol) and stirred at 0° C. for 1 hour. The reaction solution was mixed with 1-bromopentene (3.8 ml, 25 mmol) and stirred at −40° C. for 2 hours. Ethyl acetate, water and hydrochloric acid (1 N) were added to the reaction solution. The reaction product was extracted with ethyl acetate, washed with saturated brine and then dried with anhydrous sodium sulfate, and the material obtained by evaporating the solvent under a reduced pressure was separated and purified by a silica gel column chromatography to obtain 2.7 g (11 mmol, 49% in yield) of the title compound.

후처리

  1. stirringstirred at −40° C. for 2 hours
  2. extractionThe reaction product was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. customthe material obtained
  6. customby evaporating the solvent under a reduced pressure
  7. customwas separated
  8. custompurified by a silica gel column chromatography
  9. customto obtain

출처 및 근거

ORD 기록
ord-9af217dc1303420cbdc8750f4f8652a7
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06498251B1

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