HCID 21217007, compound → HCID 21217003, compound

Participants

Reaction Steps

A 250 mL 3 neck round-bottom flask equipped with a condenser was flushed with nitrogen and then loaded with diethyl 5-hexyl-2,3-di-(4-fluorophenyl)-1,4-benzenedicarboxylate (4 g, 8.1 mmol), anhydrous THF (40 mL) and then cooled in an ice/water bath. Lithium aluminum hydride (1.23 9, 32.4 mmol) followed by THF (40 mL) was added to the reaction mixture with stirring. The mixture was warmed to room temperature and then refluxed for 6 hours. This was then cooled to room temperature and the excess lithium aluminum hydride was destroyed by dropwise addition of water. NaOH (1.5 g in 10 mL of water) was then added and stirred for 15 min. The solvent was then removed by rotary evaporation and then 10% sulfuric acid (80 mL) was added to the white gelatinous product and stirred overnight. The white precipitate was filtered and washed with water and air-dried (3.12 g, 94.0% yield).

Provenance & Evidence