Aluminium lithium hydride → HCID 86696514, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(2-cyanophenyl)-N-methoxy-N-methylcyclopropanecarboxamide (250 mg, 1.086 mmol) in THF (5 mL) was stirred, maintaining the temperature below −40° C., as a suspension of LAH (82 mg, 2.171 mmol) in THF (20 mL) at −50° C. was added. After the addition was complete, the reaction was slowly allowed to warm to −30° C., and then cooled to below −40° C. The reaction was quenched with a EtOAc, followed by 1 N sodium hydroxide (1 mL). The reaction was stirred at rt for 30 min. The solution was diluted with EtOAc, filtered through celite, then concentrated. The material was purified on silica gel using 5-40% EtOAc/hexanes as the eluent to give 2-(2-formylcyclopropyl)benzonitrile (135 mg, 72.6%) as an oil. 1H NMR (400 MHz, CHLOROFORM-d) δ 9.42 (d, J=4.3 Hz, 1H), 7.67 (dd, J=7.8, 1.0 Hz, 1H), 7.56 (td, J=7.8, 1.3 Hz, 1H), 7.36 (td, J=7.6, 1.1 Hz, 1H), 7.12 (d, J=8.0 Hz, 1H), 2.95 (ddd, J=9.2, 6.6, 4.3 Hz, 1H), 2.27 (ddt, J=8.5, 5.3, 4.3 Hz, 1H), 1.87 (dt, J=9.3, 5.3 Hz, 1H), 1.67-1.49 (m, 1H). LCMS: M+1=171.1.

Provenance & Evidence