4-Nitrobenzoic Acid → HCID 178486949, compound

Participants

Reaction Steps

To a solution of triphenylphosphine (142.7 mg, 0.546 mmol) in tetrahydrofuran (2 mL) was added diisopropyl azodicarboxylate (11 mg, 0.54 mmol), and the resulting mixture was stirred at room temperature for 30 min. The mixture was cooled to −50° C. and cis-3-(4-bromo-2-methoxyphenyl)cyclobutanol (100 mg, 0.389 mmol) in tetrahydrofuran (0.5 mL) was added. The reaction was stirred for 20 min, followed by addition of solid 4-nitrobenzoic acid (90.97 mg, 0.546 mmol), the resulting mixture was warmed to room temperature and allowed to stir at room temperature for 15 hr. The reaction was then cooled to 0° C., to which was added sodium hydroxide (5 mL, 0.5 M in methanol). After 40 min the reaction was quenched with sat. ammonium chloride (5 mL), and diluted with ethyl acetate (15 mL). The organic layer was separated, dried over sodium sulfate, filtered and evaporated to dryness to give the title compound (78 mg, 54%) as an oil.

Provenance & Evidence