Sodium Bicarbonate → HCID 18614763, compound

Participants

Reaction Steps

To a solution of (87) (6.6 mg, 17.8 mmol) in 500 mL THF was added methyl magnesium bromide (10 mL, 3.0 M). The mixture was stirred at room temperature for 3 h. The mixture was poured into 5 mL dilute NaHCO3 solution. The aqueous solution was extracted with dichloromethane (5 mL×3). The organic layers were combined, washed with brine and dried with anhydrous sodium sulfate. The mixture was then chromatographed on a silica gel TLC plate using dichloromethane/ethyl acetate (9:1) to give (88): yield (32%): 1H NMR (400 MHz, CDCl3) δ 7.75 (s, 2H), 7.57 (s, 1H), 5.89 (dd, 1H, J=4.25, 56.66 Hz), 4.92 (ddd, 1H, J=4.25, 15.76, 48.17 Hz), 2.47 (br s, 1H), 1.75 (s, 3H).

Provenance & Evidence