Hydrochloric Acid → HCID 53685369, compound

Participants

Reaction Conditions

Reaction Steps

The dianion of ethyl acetoacetate was generated by adding 0.93 mL (7.3 mmoles) of purified ethyl acetoacetate to a suspension of 0.29 g (60% by weight in oil suspension, 7.3 mmoles) of sodium hydride in tetrahydrofuran (10 mL) at 0° C. under argon followed by the addition of 2.93 mL (7.3 mmoles) of 2.5M n-butyllithium. The orange solution was stirred at 0° C. for one hour then cooled to -80° C. (dry ice-acetone). The dianion solution was added to a solution of 1.01 g (2.4 mmoles) of 5,5-bis(4-fluorophenyl)-4-(5-phenyl-1H-tetrazol-1-yl)-2,4-pentadienal in 20 mL of tetrahydrofuran at -80° C. under argon. After stirring for 10 minutes, the mixture was neutralized with 4 mL of 2M HCl and 4 mL of saturated aqueous NH4Cl solution. The desired product was extracted with ethyl acetate and purified by silica gel column chromatography using a gradient elution of ethyl acetate-hexanes to yield 0.90 g (68%) of the title compound.

Provenance & Evidence