Hydrochloric Acid → HCID 11992476, compound

Participants

Reaction Steps

To a solution of ethyl({4-[(4-fluorophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}oxy)acetate 10 (0.580 g, 1.336 mmol) in anhydrous THF (25 mL) was added LiAlH4 (3.4 mL, 3.42 mmol, 1.0 M solution in THF) drop-wise under N2 atmosphere at room temperature. The resultant solution was stirred at RT for 0.5 h. The reaction mixture was quenched with EtOAc (10 mL) and continued the stirring for an additional 10 min. Reaction mixture was poured into 15% aqueous HCl (50 mL) and then extracted with EtOAc (4×30 mL). The combined organic layer was washed with brine (1×30 mL), dried (Na2SO4), and concentrated under reduced pressure to afford the crude product. The product was purified by silica gel column chromatography using hexanes: EtOAc (19:1 to 4:1) as an eluent to afford 0.41 g (79%) of the title compound (15) as white foam. 1H NMR (400 MHz, DMSO-d6): δ 7.16-7.06 (m, 4H), 7.03 (d, J=8.4 Hz, 2H), 6.84 (d, J=6.4 Hz, 2H), 4.83 (t, J=5.6 Hz, 1H), 3.92 (t, J=5.2 Hz, 2H), 3.67 (q, J1=10.8 Hz, J2=5.2 Hz, 2H), 1.90 (s, 2H), 1.86 (s, 2H), 1.24 (s, 2H), 0.87 (s, 6H), 0.87 (6H). LCMS (APCI): m/z 405 (M+Na)+.

Provenance & Evidence