Tributylphosphine → 6-[3-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenoxy]-nicotinonitrile

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

Mix 6-(3-hydroxymethyl-phenoxy)-nicotinonitrile (1.63 g, 7.18 mmol) and 1-(2,4-dihydroxy-3-propyl-phenyl)-ethanone (1.33 g, 6.84 mmol) in 2:1 toluene/dichloromethane (24 mL). Cool to −20° C. and add tributylphosphine (2.6 mL, 10.26 mmol) dropwise. After stirring for 5 minutes, add 1,1′-(azodicarbonyl)dipiperidine in three batches. Allow the reaction mixture to warm to ambient temperature overnight. Concentrate under reduced pressure to give a yellow solid. Dilute with diethyl ether (50 mL) and cool to 0° C. Filter the white precipitate and concentrate the filtrate under reduced pressure to give a residue. Purification by flash chromatography, using 5% ethyl acetate/hexanes to 30% ethyl acetate/hexanes as a gradient eluent yields the title compound (0.91 g, 33%): MS (m/z): 401.2 (M−1). 1H NMR (CDCl3) 12.78 (s, 1H), 8.50 (s, 1H), 7.97 (dd, J=2.2 Hz, 8.8 Hz, 1H), 7.62 (d, J=8.8 Hz, 1H), 7.51 (t, J=8.0 Hz, 1H), 7.36 (d, J=7.8 Hz, 1H), 7.25 (s, 1H), 7.16 (d, J=8.0 Hz, 1H), 7.09 (d, J=8.8 Hz, 1H), 6.51 (d, J=8.8 Hz, 1H), 5.22 (s, 2H), 2.72 (t, J=7.6 Hz, 2H), 2.60 (s, 3H), 1.62-1.53 (m, 2H), 0.94 (t, J=7.6 Hz, 3H).

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