tert-Butanol → HCID 45789215, compound

Participants

Reaction Conditions

Reaction Steps

3-Chloro-isonicotinic acid (3.0 g) was dissolved in tert-butanol (80 mL), diphenyl phosphoryl azide (5.24 g) and triethylamine (2.7 mL) were added and the reaction mixture was stirred at 100° C. for 5.5 h. After cooling to room temperature, the reaction mixture was concentrated in vacuum and the residue was dissolved in ethyl acetate and water. The layers were separated and the aqueous layer was 2× extracted with ethyl acetate, the combined organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuum. The residue was purified by column chromatography (silica 60, hexane/ethyl acetate 3:1, Rf=0.30) to afford 2.74 g of the title compound of the formula

Provenance & Evidence