Diisopropylamine → HCID 59504824, compound

Participants

Reaction Steps

A 2.5 molar solution of n-butyl lithium (114 mL, 285 mmol) in hexane was added to a cooled (−78° C.) solution of diisopropylamine (38.3 mL, 273 mmol) in tetrahydrofuran (300 mL). This cooled reaction mixture was then allowed to stir for 1 hour, after which time cyclopropylacetonitrile (20.8 mL, 261 mmol) was added at such a rate as to keep the temperature below −60° C. This mixture was then allowed to stir at −78° C. for 1 hour, after which time a solution of 4-cyano-benzoic acid methyl ester (40 g, 248 mmol) in tetrahydrofuran (100 mL) was added at such a rate as to keep the temperature below −60° C. This mixture was then slowly warmed to room temperature and stirred for 18 hours after which time it was quenched onto an aqueous 10% solution (weight/volume) citric acid (600 mL) and extracted with ethyl acetate (2×2500 mL). The organic extracts were washed with brine (600 mL), dried over magnesium sulphate, filtered, and evaporated under reduced pressure to give a brown oil (52.7 g, 100%). This material was used for subsequent steps without further purification. 1H NMR (400 MHz, CDCl3): δ 0.60 (m, 2H), 0.80 (m, 2H), 1.40 (m, 1H), 4.10 (d, 1H), 7.85 (d, 2H), 8.10 (d, 2H). ESCI MS m/z 243 [M−H]−

Provenance & Evidence