Formaldehyde → HCID 68722904, compound

Participants

Reaction Steps

n-BuLi (3.16 mL of a 1.6 M solution in hexanes, 4.96 mmol) was added dropwise to a −78° C. solution of 2,4,5-tribromo-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole (2.16 g, 4.96 mmol) in THF (50 mL). After 30 min, paraformaldehyde (0.74 g, 24.82 mmol) was added. The reaction mixture was warmed to RT, stirred overnight, quenched by addition of sat'd NH4Cl and extracted with EtOAc. The organic phase was dried (Na2SO4), filtered, and purified by silica gel chromatography (5-60% EtOAc/hex) to afford the title compound (0.57 g, 302%) as a clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 5.44 (d, J=0.46 Hz, 2H), 4.74-4.88 (m, 2H), 3.49-3.69 (m, 2H), 0.88-1.02 (m, 2H), −0.13-0.22 (m, 9H).

Provenance & Evidence