Pyridine → HCID 58234690, compound

Participants

Reaction Steps

To a solution of salicylaldehyde (10.39 g, 85.08 mmol) and pyridine (7.57 mL, 1.1 eq.) in dichloromethane (40 mL) in a 250 mL round-bottom flask was added a solution of 1M isopropyl chloroformate in toluene (93.60 mL, 1.1 eq.) slowly in 20 minutes to maintain the internal temperature below −25° C. using a cold bath of dry ice/acetone. White precipitate began to form during the addition and more precipitate was seen after the addition was complete. The mixture was removed from the cold bath and stirred for 2 hours with the application of a slow increase of temperature. Subsequently, the reaction mixture was evaporated to half the volume on a rotary evaporator, diluted with ethyl acetate (50 mL), washed with ice cold water (2×100 mL), 1N NaOH (3×50 mL), ice water (2×50 mL) and cold brine (1×100 mL), dried over anhydrous MgSO4 and evaporated on a rotary evaporator to produce 15.85 g (88%) of yellow oil. The carbonate (10.52 g) was distilled in high vacuum to yield 9.32 g of colorless oil (b.p. 101-103° C./0.8 torr). 1H NMR (300 MHz, CDCl3): δ10.22 (s, 1H), 7.92 (dd, J=2.1, 7.5 Hz, 1H), 7.68 (dt, J=2.1, 7.5 Hz, 1H), 7.47 (t, J=7.5 Hz, 1H), 7.32 (d, J=7.5 Hz, 1H), 5.04 (m, 1H), 1.45 (d, J=6.3 Hz, 6H).

Provenance & Evidence