Isopropyl Acetate → HCID 66770541, compound

Participants

Reaction Conditions

Reaction Steps

A 0.5 M solution of ethyl glyoxalate in toluene (0.95 ml, 5 mmol; CAS Reg. No. 924-44-7) and acetic acid (0.4 ml) were added to an ice cold solution of 3-(methylsulfonyl)aniline (500 mg, 2 mmol; CAS Reg. No. 5470-49-5) in methanol (6.3 ml) under an argon atmosphere. Sodium cyanoborohydride (356 mg, 5 mmol) was added in 3 portions within 10 min. The reaction mixture was stirred for 45 min at 0° C. and then at ambient temperature over night. The reaction mixture was poured onto ice water (100 ml). iPrOAc (100 ml) was added and the layers were separated. The aqueous layer was extracted one more time with iPrOAc (100 ml). The combined extracts were washed two times with ice water/brine 1/1 and dried over sodium sulfate. After filtering the solvent was removed under reduced pressure to give the crude product as yellow foam which was purified by column chromatography (silica gel, iPrOAc/n-heptane) to obtain the title compound (350 mg, 1 mmol; 56%) as white solid. MS (ESI): m/z=258.2 [M+H]+.

Provenance & Evidence