Sodium hydride → Ethyl 4-benzyloxy-2-methyl-6-[3-(quinolin-2-ylmethoxy)-benzyloxy]-benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 4-benzyloxy-2-hydroxy-6-methyl-benzoate (5.1 g, 16 mmol, example 63) in DMF (100 mL), with 25° C. water bath cooling, is added 60% sodium hydride emulsion (1.3 g, 32 mmol) over 2 minutes. This mixture is stirred 30 minutes with the cooling bath removed. A solution of 3-(quinolin-2-ylmethoxy)-benzyl chloride hydrochloride (5.1 g, 16 mmol, example 49), in DMF (55 mL) is added and the reaction heated at 60° C. for 6 hours. The solvent is removed in vacuo and the residue purified by flash chromatography (silica, 0.5 to 2% methanol in dichloromethane) to give the title compound. MS (ESI) 534 (M+H)+.

Provenance & Evidence