4-Nitrobenzoic Acid → HCID 66671357, compound

Participants

Reaction Steps

To a solution containing 72 (1.99 g, 5.66 mmol), p-nitrobenzoic acid (1.23 g, 7.36 mmol), and Ph3P (2.07 g, 7.92 mmol) in THF (35 mL) at 0° C. was added DIAD (1.6 mL, 8.2 mmol). After the addition was complete, the ice bath was removed and the reaction mixture was stirred at ambient temperature for 2 hat which point TLC analysis revealed complete consumption of 72 [EtOAc, Rf(72)=0.2; Rf(73)=0.6]. The solvent was removed in vacuo and the residue was dissolved in EtOAc, washed with saturated aqueous NaHCO3, brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 7 g of crude 73 which was purified by flash silica gel chromatography (20% EtOAc/hexanes) to obtained 2.68 g of 73 (95%) as a white solid 1H NMR (CDCl3, 300 MHz): δ8.3 (d, J=35 Hz, 2H), 7.6 (d, J=35 Hz, 2H), 7.2 (m, 5H), 7.0 (s, 1H), 5.2 (s, 2H), 4.4-3.2 (m, 3H), 3.0-2.9 (m, 1H), 2.2 (s, 2H), 1.9 (s, 2H) ppm.

Provenance & Evidence