Ethyl Acetate → HCID 18753700, compound

Participants

Reaction Steps

To a stirred solution of 5-[4-(t-butyl-dimethylsilanyl-oxy)cyclopent-2-en-1-yl]-9-chloro-3-methyl-5H-isoxazolo[4,3-c]quinolin-4-one (3.4 g, 7.9 mmol) in THF (60 mL) was added HF pyridine/pyridine/THF (1:2:8; 50 mL). The mixture was stirred at r.t. for 6 hours. Solid NaHCO3 (6 g) and ethyl acetate (60 mL) were added. Aqueous NaHCO3 was then added until the reaction was quenched The layers were separated and the organic fraction was washed (brine, water, aqueous CuSO4), dried (Na2SO4), filtered and concentrated. Column chromatography (silica gel, hexanes/ethyl acetate, gradient) gave desired product (2.2 g, 88%). 1H NMR (CDCl3, 400 MHz) δ; 7.59 (d, 1H); 7.37 (t, 1H); 7.30 (d, 1H); 6.15 (m, 1H); 5.91 (m, 1H); 5.78 (broad, 1H); 4.82 (broad, 1H); 2.81 (s, 3H); 2.82 (m, 1H); 2.18 (m, 1H).

Provenance & Evidence