2-Thiophenecarboxaldehyde → HCID 23284530, compound

Participants

Reaction Conditions

Reaction Steps

Under an atmosphere of argon, 1.6 M hexane (30 ml) solution of n-butyl lithium was added dropwise to a tetrahydrofuran (200 ml) solution of diisopropylamine (5.52 g, 54.7 mmol) which was cooled at -78° C., and the mixture was stirred for 30 minutes 2-Chloropyridine (5.71 g, 50.3 mmol) was added dropwise to the reaction solution, followed by 90 minutes of stirring. 2-Thiophenecarbaldehyde (6.01 g, 53.7 mmol) was added dropwise to the reaction solution, followed by 30 minutes of stirring. The reaction solution was mixed with brine and extracted with chloroform. The organic layer was washed with brine and dried over anhydrous sodium sulfate. After removing sodium sulfate by filtration, the solvent was evaporated under a reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform) to give α-(2-chloropyridin-3-yl)-2-thiophenmethanol (6.66 g, 27.5 mmol, 59%).

Provenance & Evidence