tert-Butanol → 2-Chloro-6-methyl-isonicotinic acid tert-butyl ester

참여 물질

반응 단계

A suspension of 0.2 g (1.17 mmol) 2-chloro-6-methyl-isonicotinic acid in 5 ml toluene is treated with 2 drops of DMF and 0.17 ml (2.33 mmol) SOCl2 and refluxed for 4 h. The mixture is concentrated under reduced pressure and the residue is taken up in 1.5 ml DCM, 0.22 ml tBuOH and 0.24 ml Et3N and stirred in the presence of 7 mg (0.06 mmol) DMAP for 18 h. The mixture is diluted with DCM, washed with 10% aqueous citric acid, water and 10% aqueous NaHCO3, dried with sodium sulfate and evaporated. Chromatography of the product on silica gel (hexane/EtOAc 4:1 and 3:1) yields the title compound as a yellowish solid.

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