Ethyl Acetate → HCID 118006058, compound

Participants

Reaction Steps

A mixture containing methyl 2-(4-(1H-pyrazol-1-yl)benzylidene)-3-oxopentanoate (mixture of alkene isomers, 3.5 g, 12 mmol, Intermediate 32: step a) and wet 10% palladium on carbon (2.6 g) in ethanol (123 mL) was stirred at 23° C. under an atmosphere of hydrogen gas (balloon pressure). After 2 hours, the reaction mixture was degassed by bubbling nitrogen gas through the solution. The degassed mixture was filtered through Celite®, rinsing with ethanol. The filtrate was concentrated to afford a colorless oil. Ethyl acetate (100 mL) was added. Celite® (8 g) was added to the solution and the solvent was removed by rotary evaporation to afford a free-flowing powder. The powder was loaded onto a column of silica gel for purification. Elution with hexanes initially, grading to 40% ethyl acetate-hexanes provided the title compound as a clear, colorless oil.

Provenance & Evidence