Hexanoyl chloride → 3-Hexanoyl-1-tosylindole

HRID 1636195ノート

反応式

HRID 1636195 の反応式
[Cl-].[Cl-].[Cl-].[Al+3].[C:5](Cl)(=[O:11])[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[S:13]([N:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24]1)([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14]>ClCCl>[C:5]([C:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:23]([S:13]([C:16]2[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH:24]=1)(=[O:11])[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

参加物

5

反応物 3

HCID 67340Hexanoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 10956616N-Tosylindole

生成物 1

HCID 193502863-Hexanoyl-1-tosylindole収率 78.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

反応条件

温度
5 °C

実験手順

Aluminium trichloride (6.01 g, 45.2 mmol), is suspended in dichloromethane (80 cm3), under nitrogen. A solution of hexanoyl chloride (5a) (6.62 g, 49.2 mmol) in dichloromethane (20 cm3) is added slowly to the stirred mixture at ambient temperature. After the addition is complete, the mixture is stirred for a further 10 minutes. The reaction mixture is cooled to 5° C. 1-tosylindole (4) (45.2 mmol, 12.24 g) in dichloromethane (20 cm3) is added to the mixture while the temperature is maintained at 5° C. After two hours stirring at room temperature the reaction mixture is treated with ice water, extracted with dichloromethane and dried over magnesium sulphate. Evaporation of the solvent gives a thick oil, which crystallises in the presence of methanol and dichloromethane to yield colourless crystals of 3-hexanoyl-1-tosylindole (6a) (13.07 g, 35.42 mmol, 78%), m.p. 91-93° C.

後処理

  1. additionAfter the addition
  2. temperatureis maintained at 5° C
  3. stirringAfter two hours stirring at room temperature the reaction mixture
  4. extractionextracted with dichloromethane
  5. dry with materialdried over magnesium sulphate
  6. customEvaporation of the solvent
  7. customgives a thick oil, which
  8. customcrystallises in the presence of methanol and dichloromethane

出典と根拠

ORDレコード
ord-068146c8dd3a40698e44ae94b7f5bf80
出典データセット
uspto-grants-2000_03
特許番号
US06033601

反応ノート

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