Dimethylamine → (2E)-4-(Dimethylamino)-2-butenoic acid

Participants

Reaction Steps

A solution of 211 ml of dimethylamine (2M in tetrahydrofuran, 0.422 moles) is added dropwise to a solution of 50 g trimethylsilyl-4-bromocrotonate (0.211 moles, 75.9% by GC-MS) in 250 ml of tetrahydrofuran at 0–5° C. under N2. The reaction mixture is stirred at room temperature for 30 minutes. A white solid by-product is removed by filtering and 2 ml water is added to the filtrate followed by seeding. The crystals formed are filtered and washed with ether to give 18.3 g (from two crops) of the desired product as off-white solid. Yield is 67.2% (98% purity by GC-MS, NMR is consistent with the expected structure).

Provenance & Evidence