N-Methyl-N,4-bis(methyloxy)-2-(4-methyl-1-pentyn-1-yl)benzamide → 1-[4-(Methyloxy)-2-(4-methyl-1-pentyn-1-yl)phenyl]-2-phenylethanone

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Reaction Steps

N-Methyl-N,4-bis(methyloxy)-2-(4-methyl-1-pentyn-1-yl)benzamide (103) (0.72 g, 2.62 mmol) was treated with benzylmagnesium chloride in THF to give 0.73 g (91%) of the title compound (104) as a light yellow oil. 1H NMR (400 MHz, CDCl3): δ 1.04 (d, J=6.6 Hz, 6H), 1.85-2.00 (m, 1H), 2.35 (d, J=6.6 Hz, 2H), 3.83 (s, 3H), 4.44 (s, 2H), 6.82 (dd, J1=8.8 Hz, J2=2.5 Hz, 1H), 6.98 (d, J=2.5 Hz, 1H), 7.19-7.25 (m, 3H), 7.26-7.32 (m, 2H), 7.65 (d, J=8.8 Hz, 1H). LCMS (APCI): m/z 307 (M+H)+.

Provenance & Evidence