Hexanoyl chloride → 3-Hexanoyl-1-tosylindole

HRID 1636195Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 5 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-068146c8dd3a40698e44ae94b7f5bf80
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06033601

Reaction notes

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