2-Methyl-2-butene → 6-(2-Tert-butoxy-2-oxoethoxy)-2-chloroquinoline-3-carboxylic acid

Participants

Reaction Steps

To a suspension of tert-butyl 2-(2-chloro-3-formylquinolin-6-yloxy)acetate (3.6 g, 11 mmol) in tert-butanol (150 mL) was added 2-methyl-2-butene (14.9 mL, 133 mmol) and a solution of sodium chlorite (8.27 g, 73.1 mmol) and sodium dihydrogenphosphate (8.10 g, 58.7 mmol) in water (50 mL). The reaction was allowed to stir at room temperature for 1 hour. The tert-butanol was removed in vacuo. The mixture was diluted with water (60 mL) and acidified to pH=4 with 1 N aqueous hydrochloric acid. The resulting precipitate was filtered, washed with water, and dried under vacuum to give the title compound (3.7 g, 100%) as a white solid. +ESI (M+H) 338.1; 1H NMR (400 MHz, CD3OD, δ): 8.69 (s, 1 H), 7.89 (d, J=9.19 Hz, 1 H), 7.56 (dd, J=9.19, 2.74 Hz, 1 H), 7.34 (d, J=2.93 Hz, 1 H), 4.76 (s, 2 H), 1.49 (s, 9 H).

Provenance & Evidence