Hydrochloric Acid → HCID 131730028, compound

Participants

Reaction Conditions

Reaction Steps

24 (ethyl (2E)-4-oxopent-2-enamide) (5.18 g, 36.7 mmol) is dissolved in MeOH (6 ml) and H2O (54 ml) and cooled to 0° C. NaBH4 is added to the resulting solution (426 mg, 11.3 mmol) in portions over 15 min. After 30 min of additional stirring at 0° C., the reaction mixture is acidified with 2 M HCl (1.15 ml) and extracted with AcOiPr (2×1 l). The organic phases are washed with brine (2×25 ml). The combined organic phases are dried with Na2SO4 and evaporated under reduced pressure at 40° C. The residue is purified by flash chromatography (MeOH:CH2Cl2 5:95 to 7.5:92.5) and yields 25 (rac-Ethyl (2E)-4-hydroxypent-2-enamide) (4.60 g, 88%) as a viscous brown oil.

Provenance & Evidence