Ethyl Acetate → HCID 19746239, compound

Participants

Reaction Conditions

Reaction Steps

Phosphorus oxychloride (1.61 ml, 0.0173 mol) is added dropwise to 1.34 ml of N,N-dimethylformamide (DMF) while the reaction mixture is maintained between 10° to 20° C. with an external cooling bath. A solution of N-methyl-N-phenethyl-2-(3-benzyloxyphenyl)acetamide (3.73 g, 0.0144 mol) in DMF is added dropwise, the resulting mixture is heated at 100° C. for 6 hours. After cooling to room temperature, the reaction mixture is poured into an ice/H2O mixture, ethyl acetate is added, followed by 7.3 g of sodium acetate. The resulting mixture is stirred for 1 hour. The layers are separated. The organic layer is washed with 10 ml of 1N aqueous HCl and brine; dried (MgSO4) and concentrated concentrated in vacuo. The residue obtained is purified by a flash column packed with silica gel and eluted with 5% ethyl acetate in CH2Cl2 to give N-methyl-N-phenethyl-2-(5-benzyloxy-2-formylphenyl)acetamide. NMR confirms this structure.

Provenance & Evidence