Methanol → HCID 59411458, compound

Participants

Reaction Steps

5-Nitro-isochromen-1-one (4.2 g, 0.022 mol) and serinol (2.0 g, 0.022 mol) were refluxed in methanol (40 mL, 1 mol) for 1 hour. TLC showed all the starting material consumed, triethylamine (20 mL, 0.1 mol) was added to the mixture and the reaction mixture was refluxed overnight. The volatiles were removed via rotovapor, and the residue was diluted with methylene chloride (100 mL, 2 mol). Acetic anhydride (9 g, 0.09 mol) and 4-dimethylaminopyridine (30 mg, 0.0002 mol) were then added and the mixture was stirred at room temperature overnight. The volatiles were removed and the residue was purified via flash column chromatography (120 g of silica gel, 0-50% EtOAc/Hexane) to give a yellow oil. MS m/z (M+H) 349.1.

Provenance & Evidence