Diethyl Ether → HCID 66678440, compound

Participants

Reaction Conditions

Reaction Steps

A solution of methyllithium in Et2O (1.6M, 6.8 mL, 10.9 mmol) was added dropwise into a solution of 4-bromo-2′-methylbiphenyl-2-carbaldehyde (2.0 g, 7.3 mmol) in anhydrous THF (30 mL) cooled at −78° C. under nitrogen atmosphere. The resulting mixture was stirred at −78° C. for 45 minutes and an additional amount of methyllithium in Et2O (1.6M, 3.4 mL, 5.5 mmol) was added. After 10 minutes, iodomethane (4.1 ml, 65.4 mmol) was added. The cooling bath was removed and the reaction mixture was stirred at RT for 5 days. The reaction mixture was diluted with MTBE (100 mL), and then washed with water (2×50 mL) and brine (50 mL). The aqueous layers were extracted with MTBE (100 mL). The organic layers were combined, dried (MgSO4) and concentrated under vacuum. After purification by flash chromatography (silica, heptane/MTBE), the title compound was obtained as a pale yellow oil (1.90 g, 86%). HPLC (Method A) Rt 5.7 min (Purity: 91%). 1H NMR (DMSO-d6, 300 MHz) δ 7.62 (d, J=2.2 Hz, 0.4H), 7.59 (d, J=2.2 Hz, 0.6H), 7.52 (dd, J=8.1, 2.2 Hz, 1H), 7.35-7.21 (m, 3H), 7.13-7.02 (m, 2H), 4.05 (q, J=6.4 Hz, 0.4H), 3.84 (q, J=6.4 Hz, 0.6H), 3.05 (s, 1.2H), 3.03 (s, 1.8H), 2.03 (s, 1.8H), 1.98 (s, 1.2H), 1.17 (d, J=6.4 Hz, 1.8H), 1.11 (d, J=6.4 Hz, 1.2H).

Provenance & Evidence