Acetic acid, 2,2-dimethoxy-, methyl ester → N-(2,5-dichlorobenzyl)-2,2-dimethoxyacetamide

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Reaction Steps

A solution of methyl dimethoxyacetate (0.823 g, 6.08 mmol) and 2,5-dichlorobenzylamine (1.0 g, 5.7 mmol) was heated to 90° C. in a sealed tube for 48 h. The crude material was purified by column chromatography on silica gel [eluting with 40% EtOAc in hexanes] to afford the title compound as a clear oil. 1H NMR (400 MHz, CDCl3) δ=3.41 (s, 6H), 4.53 (d, J=6.6 Hz, 2H), 4.75 (s, 1H), 7.19-7.23 (m, 1H), 7.30 (d, J=8.4 Hz, 1H), 7.35 (d, J=2.5 Hz, 1H). MS (ES+): m/z=278/280/282 [MH+]. HPLC: tR=3.03 min (ZQ2, polar—5 min).

Provenance & Evidence