Triethylamine → 3-[3-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenylsulfanyl]-benzonitrile

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Reaction Steps

Add methanesulfonyl chloride (0.119 g, 1.04 mmol) to a solution of 3-(3-hydroxymethyl-phenylsulfanyl)-benzonitrile (0.250 g, 1.04 mmol) and triethylamine (0.210 g, 2.07 mmol) in dichloromethane (0.2 M). Stir for 1 h. Evaporate solvent. Dissolve the residue in N,N-dimethylformamide and add 1-(2,4-dihydroxy-3-propyl-phenyl)-ethanone (0.201 g, 1.04 mmol). Add cesium carbonate (0.673 g, 2.07 mmol) and stir for 1 h at 60° C. Dilute the reaction mixture with diethyl ether and wash with water (3×). Purify the residue by flash chromatography, eluting with hexanes, ramping to 50% ethyl acetate/hexanes to elute the title compound (0.331 mg, 0.790 mmol, 76%): MS (m/z): 416 (M−1).

Provenance & Evidence