Diisopropylamine → 2-Acetyl-4-(4-pyridyl)cyclohexanone

Participants

Reaction Conditions

Reaction Steps

3.2 ml of diisopropylamine was dissolved in 40 ml of tetrahydrofuran and 14.2 ml of a 1.6 M solution of n-butyllithium in hexane was added thereto at -20° C. A solution prepared by dissolving 2 g of 4-(4-pyridyl)cyclohexanone in 40 ml of tetrahydrofuran was further added thereto at -40° C. The obtained reaction mixture was cooled to -78° C. and 2.5 g of acetylimidazole dissolved in 40 ml of tetrahydrofuran was added thereto. After stirring at room temperature, the reaction mixture was poured onto ice water and washed with ether. The aqueous phase was saturated with ammonium chloride and extracted with methylene chloride to give 1.65 g of 2-acetyl-4-(4-pyridyl)cyclohexanone. NMRδTMSCDCl3 : 1.7-2.2 (3H, m), 2.16 (3H, s), 2.3-2.6 (3H, m), 2.6-2.9 (1H, m), 7.10 (2H, dd), 8.55 (2H, dd) and 15.7 (1H, s).

Provenance & Evidence