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

HRID 2301132ノート

反応式

HRID 2301132 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9af217dc1303420cbdc8750f4f8652a7
出典データセット
uspto-grants-2002_12
特許番号
US06498251B1

反応ノート

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