[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8](Cl)=[O:9])=[CH:4][CH:3]=1.[CH3:11][C:12]([CH3:16])([CH3:15])[CH2:13][OH:14]>C1(C)C=CC=CC=1.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([O:14][CH2:13][C:12]([CH3:16])([CH3:15])[CH3:11])=[O:9])=[CH:4][CH:3]=1To a solution of 10 g (56.8 mmol) of 6-chloropyridine-3-carbonyl chloride in 100 mL of anhydrous toluene are added under argon, at room temperature, 15 g (170.4 mmol) of 2,2-dimethylpropanol. The reaction medium is then heated for 6 hours at 80° C. After cooling to room temperature, the medium is concentrated and the residue obtained is taken up in 800 mL of EtOAc, washed successively with water (2×200 mL), saturated NaHCO3 solution (2×200 mL) and brine (100 mL), dried over Na2SO4, and then concentrated under reduced pressure and purified by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAc gradient of 0 to 5% EtOAc. 11.9 g of 2,2-dimethylpropyl 6-chloropyridine-3-carboxylate are obtained in the form of a white powder.
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