Sulfamic Acid → 2-Methoxy-3'-carboethoxy-[1,1'-biphenyl]-6-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

Aldehyde 4a (0.512 g., 1.80 mmol, 1 equiv.) is dissolved in 17 mL of THF and 13 mL of H2O. The solution is cooled to 0° C. Sulfamic acid (0.525 g., 5.41 mmol, 3 equiv. ) is then added, followed by a solution of sodium chlorite (80% tech., 0.612 g., 5.41 mmol, 3 equiv. ) in 4 mL of H2O. The mixture is stirred for 15 min. at 0° C., and then poured into EtOAc and water. The aqueous layer is extracted thrice with EtOAc, and the combined organic-phase is washed with brine. The organic phase is dried (MgSO4) and then concentrated in vacuo to afford 2-methoxy-3'-carboethoxy-[1,1'-biphenyl]-6-carboxylic acid (5a) as a pale yellow oil (0.583 g., 1.80 mmol, 100%): 1H NMR (300 MHz, CDCl3) δ 10.17 (br, 1H, C2H), 8.02 (ddd, J=2, 2, 8 Hz, 1H, ArH), 7.94 (s, 1H, ArH), 7.56 (d, J=8 Hz, 1H, ArH), 7.41 (m, 3H, ArH), 7.15 (d, J=8 Hz, 1H, ArH), 4.19 (q, J=7 Hz, 2H, CO2CH2), 3.,73 (s, 3H, OCH3), 1.39 (t, J=7 Hz, 3H, CH2CH3).

Provenance & Evidence