Ethyl Acetate → HCID 67983767, compound

Participants

Reaction Conditions

Reaction Steps

Lithium aluminum hydride (1M in tetrahydrofuran, 29 mL, 29 mmol, 2.5 eq) was added to a dry three-necked flask filled with nitrogen and cooled to 0° C. Methyl 5-cyclopropyl-3-(o-tolyl)isoxazole-4-carboxylate (3.02 g, 11.7 mmol) was dissolved in tetrahydrofuran (40 mL) and added dropwise to the flask, ensuring that the internal temperature remained below −10° C. The mixture was stirred for an hour, then ethyl acetate (1.3 mL) was added dropwise, keeping the temperature below 0° C. followed by water (1.3 mL), taking care that the mixture was vigorously stirring at all times. Sodium hydroxide solution (3.9 mL, 15% solution by weight) was added dropwise and the mixture stirred vigorously for a further 30 minutes, warming up to RT. The mixture was filtered through a CELITE® pad, which was washed with ethyl acetate (120 mL). The organics were washed with water (100 mL) and brine (75 mL) then dried over magnesium sulfate and concentrated under vacuum and purified by column chromatography (SiO2, linear gradient, 0-100% ethyl acetate in hexanes) to afford the desired product. 1H-NMR (MeOH-d4, 400 MHz) δ 7.41-7.26 (m, 4H), 4.36 (s, 2H), 2.34-2.27 (m, 1H), 2.26 (s, 3H), 1.19-1.15 (m, 4H), MS m/z 230.0 (M+1).

Provenance & Evidence