Benzyl Bromide → Benzyl 4,5-bis(benzyloxy)pyridine-2-carboxylate

Participants

Reaction Steps

21.5 g (156 mmol) of potassium carbonate was added to a suspension of 29.4 g (120 mmol) of 1,4-dihydro-5-(phenylmethoxy)-4-oxo-2-pyridinecarboxylic acid in 350 ml of N,N-dimethylformamide (DMF) and stirred for 1 hour at room temperature. 31 ml (264 mmol) of benzylbromide was added and the mixture was heated at 100° C. under stirring for 25 hours. After cooling to room temperature, the DMF was distilled off in vacuo and the residue triturated with ethyl acetate with short heating to 60° C. 40 g of inorganic salts were filtered off, the filtrate was concentrated to ca. 75 ml and chromatographed on silica gel with ethyl acetate:petroleum ether 90:10 as eluent. Yield: 35.5 g; melting point 116.7° C.

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