Acetic Anhydride → HCID 68182233, compound

Participants

Reaction Steps

To a solution of methyl 2-(3,4-dimethoxyphenyl)-3-(5-methoxyquinolin-3-yl)propanoate CCH 34144-5 (46 mg, 121 μmol) in acetic anhydride (2.0 mL, 21.2 mmol) at 0° C. in a 50 mL round-bottomed flask equipped with a magnetic stirrer was added HClO4 (ca. 70% solution in water, 0.1 mL, 1.2 mmol). The reaction mixture was then allowed to warm up to RT, stirred for 45 min and diluted with Et2O (40 mL). The solid was filtered and washed several times with Et2O giving a brown residue. The residue was then suspended in CH2Cl2 (40 mL) before neutralisation with saturated aqueous NaHCO3 solution. The organic phase was isolated, washed with brine (10 mL), dried over Na2SO4, filtered and concentrated at 40° C. under vacuum. Purification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 0:100) gave methyl 2-(2-acetyl-4,5-dimethoxyphenyl)-3-(5-methoxyquinolin-3-yl)propanoate CCH 34154 as a yellow solid (30 mg, 59% yield).

Provenance & Evidence