Diisopropylamine → HCID 23284497, compound

Participants

Reaction Conditions

Reaction Steps

Diisopropylamine (23 ml, 175 mmol) was added to a tetrahydrofuran (500 ml) solution of 1.6 M hexane solution (100 ml, 160 mmol) of n-butyl lithium at -65° C. or lower, and the mixture was warmed up to -40° C. The reaction solution was mixed with 2-chloropyridine (17 g, 150 mmol) at -70° C. or lower and stirred for 1.5 hours at -70° C. or lower. the reaction solution was mixed with cyclohexanecarbaldehyde (17 g, 151 mmol) at -70° C. or lower and stirred for 2 hours at -70° C. or lower. The reaction solution was mixed with water, warmed to room temperature and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under a reduced pressure. Thereafter, the resulting residue was purified by silica gel column chromatography (chloroform) to give 2-chloro-α-cyclohexyl-3-pyridinemethanol-(17 g, 50%).

Provenance & Evidence