Hydrochloric Acid → HCID 11452260, compound

Participants

Reaction Steps

A solution of ethyl({4-[(4-fluorophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}oxy)acetate (10) (0.290 g, 0.68 mmol) in THF/EtOH (1:1, 8 mL) was treated with 1 N NaOH (4 mL) at 70° C. for 1 h. The reaction mixture was acidified with 20% aqueous HCl, and then extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), and concentrated under reduced pressure to afford the crude product. The product was purified by flash column chromatography with chloroform and methanol as an eluent to afford 0.250 g (95%) of the title compound 11 as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 7.19-7.14 (m, 2H), 7.13 (d, J=9.3 Hz, 2H), 7.07 (d, J=8.4 Hz, 2H), 6.83 (d, J=8.7 Hz, 1H), 6.84 (d, J=8.7 Hz, 2H), 4.63 (s, 2H), 1.93 (s, 2H), 1.88 (s, 2H), 1.27 (s, 2H), 0.90 (s, 12H). LCMS (ESI): m/z 395 (M−H)−.

Provenance & Evidence