Pyridine → HCID 131730031, compound

Participants

Reaction Steps

27 (rac-Diethyl (2E)-4-hydroxypent-2-enamide) (1.05 g, 6.0 mmol), pyridine (969 μl, 12 mmol) and DMAP (147 mg, 0.60 mmol) are dissolved in toluene (30 ml) and THF (10 mL) and cooled to 0° C. Chloroacetylchloride (954 μl, 12 mol) in toluene (4 ml) is added dropwise under stirring at ≦2° C. over 15 min. The reaction mixture is stirred 2.5 h at 0° C. The resulting suspension is then poured onto H2O (50 ml) and extracted with tBuOMe (150 and 75 ml). The organic phases are washed with 1 M HCl (50 ml), H2O (50 ml), saturated NaHCO3 (50 ml) and brine (50 ml) successively. The combined organic phases are dried with Na2SO4 and evaporated under reduced pressure at 40° C. The residue is filtered with tBuOMe (50 ml) and tBuOMe:AcOEt 50:50 (300 ml) over SiO2 (15 g) and yields 34 (rac-Diethyl (2E)-4-(chloroacetoxy)pent-2-enamide) (1.46 g, 98%) as a yellow oil.

Provenance & Evidence