Dimethylamine → (2E)-4-(Dimethylamino)-2-butenoic acid
Reaction equation
[CH3:1][NH:2][CH3:3].C[Si]([O:8][C:9](=[O:14])/[CH:10]=[CH:11]/[CH2:12]Br)(C)C>O1CCCC1>[CH3:1][N:2]([CH3:3])[CH2:12]/[CH:11]=[CH:10]/[C:9]([OH:8])=[O:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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).