2-(1-Hexyn-1-yl)-N-methyl-N-(methyloxy)benzamide → 1-[2-(1-Hexyn-1-yl)phenyl]-2-[4-(methyloxy)phenyl]ethanone

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2-(1-Hexyn-1-yl)-N-methyl-N-(methyloxy)benzamide (158) (0.50 g, 2.04 mmol) was treated with 4-methoxy benzylmagnesium chloride in THF at 40° C. to give 0.43 g (69%) of the title compound (159) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 0.93 (t, J=7.2 Hz, 3H), 1.40-1.53 (m, 2H), 1.56-1.65 (m, 2H), 2.45 (t, J=7.0 Hz, 2H), 3.78 (s, 3H), 4.36 (s, 2H), 6.83 (d, J=8.5 Hz, 2H), 7.14 (d, J=8.5 Hz, 2H), 7.26-7.30 (m, 1H), 7.33-7.39 (m, 1H), 7.44-7.50 (m, 2H). LCMS (ESI): m/z 307 (M+H)+.

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