Triethylamine → HCID 67781535, compound

Participants

Reaction Steps

To a solution of 1-(2-bromo-4-methylphenyl)-2-diazoethanone (A83) (667 mg, 2.79 mmol) in THF (4.3 mL) and MeOH (4.3 mL) was added a solution of silver benzoate (96 mg, 0.42 mmol) in Et3N (1.13 mL, 11.2 mmol). The resulting mixture was stirred for 2 hours at room temperature then passed through a plug of silica gel eluting with 50% EtOAc in petroleum benzine 40-60° C. The eluent was evaporated in vacuo and the residue was adsorbed onto silica gel and separated using silica gel column chromatography (Biotage Isolera, 25 g SiO2 cartridge, 0-50% EtOAc in petroleum benzine 40-60° C.) to give the title compound A84 as a clear oil (678 mg, >99%); 1H NMR (400 MHz, CDCl3) δ 7.39 (d, J=0.7 Hz, 1H), 7.16 (d, J=7.8 Hz, 1H), 7.07 (dd, J=7.7, 1.0 Hz, 1H), 3.76 (s, 2H), 3.70 (s, 3H), 2.30 (s, 3H). LCMS-A: rt 6.070 min.

Provenance & Evidence