Ethyl Acetate → 1-phenyl-5-(2,4,5-trifluorophenyl)-1H-pyrazole-4-carbaldehyde

Temperature

50 °C

To a solution of ethyl 1-phenyl-5-(2,4,5-trifluorophenyl)-1H-pyrazole-4-carboxylate (459 mg, 1.325 mmol) in THF (5 mL) was added LAH (1.988 mL, 1.988 mmol as a 1 M THF solution) at room temperature and the reaction was then heated at 50° C. for 2 hours. The reaction was quenched with addition of 0.2 mL of water, 0.2 mL of 0.5 N NaOH and then 0.2 mL of water. The suspension was diluted with ether and was filtered through celite. Upon removal of the volatiles, the crude residue was purified by flash chromatography to afford an oil. The oil was then dissolved in 5 mL of CH2Cl2 and Dess-Martin periodinane (233.8 mg, 0.768 mmol) was added. The suspension was stirred at room temperature for 16 hours. The mixture was poured into EtOAc and was washed with brine. The organic phase was dried with Na2SO4, filtered and concentrated. The crude residue was purified by flash chromatography using a gradient of ethyl acetate/hexanes to afford the title intermediate as white solid.

1. customThe reaction was quenched with addition of 0.2 mL of water, 0.2 mL of 0.5 N NaOH
2. additionThe suspension was diluted with ether
3. filtrationwas filtered through celite
4. customUpon removal of the volatiles
5. customthe crude residue was purified by flash chromatography
6. customto afford an oil
7. washwas washed with brine
8. dry with materialThe organic phase was dried with Na2SO4
9. filtrationfiltered
10. concentrationconcentrated
11. customThe crude residue was purified by flash chromatography

ORD record

ord-e874e09684ad430185186aa98612fc67

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08742110B2