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ChemicalBook CAS DataBase List 5-Acetylindole
53330-94-2

5-Acetylindole synthesis

13synthesis methods
Indole-5-carboxylic acid

1670-81-1

Methyllithium

917-54-4

5-Acetylindole

53330-94-2

Methyl lithium (1.6 M ether solution, 30 mL, 51.2 mmol) was added slowly and dropwise to a solution of anhydrous tetrahydrofuran (30 mL) of indole-5-carboxylic acid (2.5 g, 15.5 mmol) at 0 °C and under nitrogen protection. The reaction mixture was stirred at room temperature for 4 hours before the reaction was quenched with aqueous ammonium chloride solution and extracted with dichloromethane (3 x 50 mL). The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 5-acetylindole (1.8 g, white solid).

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Yield: 87.97%

Reaction Conditions:

in tetrahydrofuran at 0; for 12 h;Inert atmosphere;

Steps:

4.1.15. The synthesis of intermediate 29
The 1H-indole-5-carboxylic acid (1.5 g, 9.31 mmol) was dissolvedin THF under Ar atmosphere and CH3Li (1.5 M, 20.48 mL,30.71 mmol) was added dropwise at 0 °C. After stirring for 12 h, thereactionwas quenched with water, extracted with EA (3 x 150 mL), and the combined organic layers were then washed with brine,dried over anhydrous Na2SO4, and concentrated in vacuo to providethe crude product, which was purified by column chromatographywith petroleum/ethyl acetate (4: 1) to give 29 (1.30 g, 87.97%) as ayellow oil. The spectra data were consistent with the literature [29].

References:

Shuai, Wen;Li, Xinnan;Li, Wenlong;Xu, Feijie;Lu, Lixue;Yao, Hong;Yang, Limei;Zhu, Huajian;Xu, Shengtao;Zhu, Zheying;Xu, Jinyi [European Journal of Medicinal Chemistry,2020,vol. 197,art. no. 112308]

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