Acetyl chloride → Diisopropylether methanol

HRID 276911

反応式

HRID 276911 の反応式
[C:1](Cl)(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[NH:9]1[C:17]2[CH:16]=[CH:15][CH:14]=[C:13]3[CH2:18][CH2:19][CH2:20][CH:11]([C:12]=23)[C:10]1=[O:21].[CH:22]([O:25][CH:26]([CH3:28])[CH3:27])([CH3:24])[CH3:23]>C(OCC)(=O)C.C(=S)=S>[CH3:1][OH:3].[CH:22]([O:25][CH:26]([CH3:28])[CH3:27])([CH3:24])[CH3:23].[C:1]([C:14]1[CH:15]=[CH:16][C:17]2[NH:9][C:10](=[O:21])[CH:11]3[CH2:20][CH2:19][CH2:18][C:13]=1[C:12]=23)(=[O:3])[CH3:2]

参加物

8

反応物 4

HCID 6367Acetyl chlorideHCID 7914Diisopropyl EtherHCID 5993752a,3,4,5-Tetrahydrobenzo[cd]indol-2(1H)-oneHCID 6451240Aluminum(III) Chloride

生成物 2

HCID 21882575Diisopropylether methanolHCID 226295716-Acetyl-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

試薬・触媒・溶媒 2

HCID 6348Carbon Disulfide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

A 3.1 ml (43.4 mmol) portion of acetyl chloride was added to a carbon disulfide suspension (100 ml) of aluminum chloride (11.5 g, 86.7 mmol) and stirred at a room temperature for 30 minutes. Thereto was added dropwise a carbon disulfide solution (150 ml) of 2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one (5.0 g, 28.9 mmol) spending 2 hours. After 2 hours of heating under reflux and confirmation of the disappearance of the material by a thin layer chromatography, this was returned to a room temperature and mixed with isopropyl ether. The supernatant fluid was discarded by decantation, and the remaining rubber-like substance was dissolved in ethyl acetate and washed with water. The water layer was extracted with ethyl acetate, the organic layers were combined and dried (Na2SO4), and then the solvent was evaporated under a reduced pressure. By recrystallizing the thus obtained oily substance from ethyl acetate-isopropyl ether and then from methanol-isopropyl ether, 3.5 g of the title compound was obtained (yield, 56%).

後処理

  1. waitspending 2 hours
  2. temperatureAfter 2 hours of heating
  3. temperatureunder reflux
  4. customthis was returned to a room temperature
  5. washwashed with water
  6. extractionThe water layer was extracted with ethyl acetate
  7. dry with materialdried (Na2SO4)
  8. customthe solvent was evaporated under a reduced pressure
  9. customBy recrystallizing the thus obtained oily substance from ethyl acetate-isopropyl ether

出典と根拠

ORDレコード
ord-22f89a4c340e44188cc12853f30910b2
出典データセット
uspto-grants-2002_03
特許番号
US06355642B1

関連ノート

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