Sulfuric Acid → HCID 66748835, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 68A (3.0 g, 18.2 mmol) in ether (70 mL) was added dropwise phenyl magnesium bromide (9.0 mL, 3.0 M solution in diethyl ether, 27.4 mmol). The mixture was heated to 60° C. and stirred at this temp for 1 hour after addition was completed. The reaction mixture was cooled to ambient temperature. The resulting dark yellow solution was poured onto crushed ice and the pH was adjusted to about 5-6 with the addition of 20% H2SO4. The mixture was extracted with ethyl acetate/diethyl ether (1:1) (50 mL×2). The combined organic layers were washed with water and brine sequentially, dried over Na2SO4, filtered, and concentrated. The crude product was purified by reserve-phase C18 column chromatography (eluted with H2O/MeOH=1:4) to afford the desired compound (3.7 g, 15.2 mmol, 83.6%). LC-MS: m/e=261.1 (M++18). 1H NMR (400 MHz, CDCl3), 6 (ppm): 7.36-7.23 (m, 5H), 4.00 (q, J=6.8, Hz, J2=14.4 Hz, 2H), 3.91 (s, 1H), 2.80-2.73 (m, 1H), 2.65-2.55 (m, 3H), 2.21-2.07 (m, 1H), 1.99-1.88 (m, 1H), 1.05 (t, J=7.2 Hz, 3H).

Provenance & Evidence