Sodium hydride → HCID 86696500, compound

Participants

Reaction Steps

In a 1 L three neck flask, DMSO (100 mL) was rapidly stirred as 60% sodium hydride in mineral oil (4.59 g, 115 mmol) was added in 1.5 g portions. After the foaming subsided, trimethylsulfoxonium iodide (25.2 g, 115 mmol) was added portion wise over a 1 h period, maintaining the temperature below 35° C. The reaction was stirred at rt for 30 min. A soln of (E)-3-(4-fluorophenyl)-N-methoxy-N-methyl acrylamide (8 g, 38.2 mmol) in DMSO (50 mL) was then added dropwise maintaining the temperature below 35° C. After 45 min, the reaction was then slowly quenched with sat'd ammonium chloride (25 mL). The solution was then diluted with EtOAc. The solution was washed with water, dried with brine, dried over magnesium sulfate, and concentrated to give trans-2-(4-fluorophenyl)-N-methoxy-N-methylcyclopropanecarboxamide as a clear oil (8.1 g, 95%). 1H NMR (400 MHz, CHLOROFORM-d) δ 7.16-7.08 (m, 2H), 7.05-6.93 (m, 2H), 3.72 (s, 3H), 3.26 (s, 3H), 2.55-2.45 (m, 1H), 1.64 (ddd, J=9.2, 5.1, 4.3 Hz, 1H), 1.34-1.29 (m, 2H). LCMS: M+1=224.16.

Provenance & Evidence