Bromoacetonitrile → HCID 57446165, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-acetyl-2,5-dimethyl-hex-4-enoic acid ethyl ester (1.0 g, 4.71 mmol) in anhydrous tetrahydro furan (30 mL) was treated with a 1.0 M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (5.2 mL, 5.18 mmol) at −78° C. The reaction mixture was stirred at −78° C. for 30 min and was then added via cannula to a solution of bromoacetonitrile (which was stirred for 30 min over basic aluminum oxide, filtered and used fresh in the reaction) in anhydrous tetrahydrofuran (5 mL) cooled to −78° C. The reaction mixture was stirred at −78° C. for 1 h, before it was allowed to warm to 25° C. and quenched by pouring it over ice in a 1.0 M aqueous hydrochloric acid solution. The mixture was extracted with ethyl acetate (3×100 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. Further purification by flash column chromatography (ISCO RediSep column, 0 to 40% ethyl acetate in hexanes) afforded the desired product, 2-(3-cyano-propionyl)-2,5-dimethyl-hex-4-enoic acid ethyl ester (0.71 g, 71%), as an oil. 1H NMR (400 MHz, CDCl3) δ: 1.28 (3H, t, J=7.0 Hz), 1.36 (3H, s), 1.63 (3H, s), 1.70 (3H, s), 2.52-2.62 (4H, m), 2.76-2.91 (2H, m), 4.20 (2H, q, J=7.0 Hz), 4.91-4.95 (1H, m). LC-MS (ESI) calcd for C14H21NO3: 251.15, found 252.3 [M+H+].

Provenance & Evidence