Water → 2-[3-(Quinolin-2-ylmethoxy)-benzyloxy]-benzaldehyde

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Reaction Steps

2-(3-Chloromethyl-phenoxymethyl)-quinoline (371 mg, 1.3 mmol, example 49) and salicylaldehyde (133 μL, 1.25 mmol) are dissolved in acetone (10 mL). K2CO3 (525 mg, 3.75 mmol) is added and the contents are heated to reflux for 16 hrs. The reaction is cooled to r.t., poured into water (100 mL) and extracted with ethyl ether (3×50 mL). The ether layers are combined and washed with Brine (3×75 mL) and dried over MgSO4. The crude material is preadsorbed onto silica gel and purified by flash chromatography (silica, 20 to 25% ethyl acetate in hexanes) to give the title compound. MS (ion spray) 370 (M+H)+.

Provenance & Evidence