Ethyl Acetate → HCID 22022391, compound

Participants

Reaction Steps

A solution of 3-bromopyridine (1.0 g, 6.33×10−3 mol) was cooled to −78° in a dry ice/acetone bath. To this solution, BuLi (3.48 mL, 6.96×10−3 mol, 2M solution in cyclohexane) was added dropwise and the reaction was stirred for 15 minutes. A solution of 1-(2-trimethylsilanylethoxymethyl)-1H-imidazole-4-carbaldehyde (0.955 g, 4.22×10−3 mol) in ether (5 mL) was added dropwise to the reaction and the solution was stirred for 1 hour at −78 C. The reaction was quenched with sat. NaHCO3 (10 mL) and allowed to warm to room temperature. Ethyl acetate was added (100 mL) and the organic layer was washed with water (3×50 mL), dried over MgSO4, filtered and solvent was removed under reduced pressure. The crude product was purified by silcagel column chromatography eluting with a gradient of ethyl acetate:hexane (1:3) to ethyl acetate to ethyl acetate:methanol (9:1). The pure product was isolated as a mixture of isomers (yellow oil, yield 778 mg, 40%). Rf 0.5 (ethyl acetate); 1H-NMR (CDCl3) δ−0.09-0.11 (m, 9H), 0.86-0.99 (m, 2H), 3.41-3.57 (m, 2H), 5.22 & 5.26 (2×s, 2H), 5.89 & 6.05 (2×s, 1H), 6.63 & 6.80 (2×s, 1H), 7.25-7.39 (m, 1H), 7.53 & 7.58 (2×s, 1H), 7.79-7.90 (m, 1H), 8.53 & 8.57 (d, 1H), 8.64 & 8.69 (2×s, 1H); ESMS Calcd (C10H18N2O2Si): 226.11, found 227.1 (M+H)+.

Provenance & Evidence