Acetone → HCID 22716743, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 2,5-dibromopyridine (5.12 g, 1 eq) in ether at −78° C., was added n-butyllithium in hexane (1.05 eq) slowly. The resulting yellow-orange precipitate was stirred 30 min. Then acetone (1.54 mL, 1.05 eq) was added. The solution was kept at −78° C. for another 30 min. n-Butyllithium in hexane (1.1 eq) was slowly syringed to the resulting orange suspension. The suspension was then stirred 1 h at −78° C. Following this, 4-(methylthio)benzaldehyde (2.85 ml, 1.1 eq.) was added. The resulting suspension was warmed to −35° C. and quenched with a solution of NH4Cl (sat.). Water and EtOAc were added and the organic layer dried over MgSO4, evaporated and purified by flash chromatography (EtOAc) to give [5-(1-Hydroxy-1-methylethyl)-2-pyridinyl][4-(methylthio)phenyl]methanol.

Provenance & Evidence