Acetyl chloride → HCID 22995208, Verbindung

Beteiligte Stoffe

Reaktionsschritte

Octylbenzene is acetylated with acetyl chloride in dichloromethane under AlCl3 catalysis and the resulting 4-octylacetophenone is converted into the corresponding oxime with hydroxylamine hydrochloride in ethanol/triethylamine. The oxime is dissolved in tetrahydrofuran under an inert gas atmosphere and doubly deprotonated with 2 equivalents of n-butyllithium. The solution is admixed with 0.5 equivalents of methyl 5-butyl-2-thiophenecarboxylate (obtained from 2-butylthiophene by lithiating with n-butyllithium in THF and reacting with carbon dioxide followed by esterification with methanol) and allowed to warm up to room temperature. Customary work-up followed by purification by recrystallization affords 5-(5-butylthiophen-2-yl)-3-(4-octylphenyl)-isoxazole; X 60 N 56 I.

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