Carbon Dioxide → HCID 58066348, compound

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyllithium in pentane (1.5M, 8.05 mL, 12.1 mmol) was added into anhydrous Et2O (40 mL) cooled at −78° C. under nitrogen atmosphere. Then a solution of 1-(4-bromo-2′-methylbiphenyl-2-yl)ethyl methyl ether (1.84 g, 6.03 mmol) in anhydrous Et2O (10 mL) was added dropwise over 10 minutes. The resulting mixture was stirred at −78° C. for 25 minutes, and then a large excess of dry ice was added and the cooling bath was removed. The reaction mixture was stirred until the temperature came back at RT, then diluted with water (20 ml) and a 5N aqueous solution of NaOH (0.5 mL). The layers were separated and the aqueous layer was washed with Et2O (20 ml). The organic layers were extracted with a 0.1N aqueous solution of NaOH (20 mL). The combined aqueous layers were acidified with a 5N aqueous solution of HCl (until pH˜1) and extracted with MTBE (2×50 mL). The organic layers were washed with brine (30 mL), combined, dried (Na2SO4) and concentrated under vacuum to give a pale yellow solid. After crystallization from a mixture of Et2O and heptane, the title compound was obtained as a white powder. HPLC (Method A) Rt 4.2 min (Purity: 98.2%). LC/MS (Method B): 269.1 (M−H)−. 1H NMR (DMSO-d6, 300 MHz) δ 13.03 (s, 1H), 8.09 (d, J=1.8 Hz, 0.4H), 8.07 (d, J=1.8 Hz, 0.6H), 7.89 (dd, J=7.9, 1.8 Hz, 1H), 7.36-7.24 (m, 3H), 7.22 (d, J=7.9 Hz, 0.4H), 7.20 (d, J=7.9 Hz, 0.6H), 7.13 (d, J=6.9 Hz, 0.4H), 7.07 (d, J=6.9 Hz, 0.6H), 4.12 (q, J=6.4 Hz, 0.4H), 3.92 (q, J=6.4 Hz, 0.6H), 3.05 (s, 1.2H), 3.04 (s, 1.8H), 2.03 (s, 1.8H), 1.98 (s, 1.2H), 1.19 (d, J=6.4 Hz, 1.8H), 1.13 (d, J=6.4 Hz, 1.2H).

Provenance & Evidence