Lithium Chloride → HCID 24830537, compound

Participants

Reaction Steps

Methyl magnesium bromide (32.4 mL of a 1.4 M solution in THF:toluene (25:75)) was added to a stirred solution of lithium chloride (1.93 g, 45.4 mmol) and 4z (11.7 g, 22.7 mmol) in THF (70 mL) at 0° C. After approximately 1 h at 0° C., the reaction was quenched by the dropwise addition of 1.0 M hydrochloric acid, and the resulting mixture stirred for 15 min. The resulting mixture was poured slowly into saturated aqueous sodium bicarbonate and extracted with EtOAc. The combined organic extracts were washed with brine, dried (magnesium sulfate) and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel (gradient elution; 35%-75% EtOAc/hexanes as eluent) to furnish the title compound 4e. m/z (ES) 533 (MH)+. 1HNMR (500 MHz, CDCl3): δ 9.23 (d, 1H, J=2.1 Hz), 8.95 (s, 2H), 8.39 (dd, 1H, J=2.3, 8.5 Hz), 7.89 (d, 1H, J=9.0 Hz), 7.79 (d, 1H, J=8.9 Hz), 7.57 (m, 4H), 7.46 (d, 1H, J=8.5 Hz), 5.92 (s, 2H), 4.20 (s, 1H), 3.22 (m, 1H), 2.38 (s, 6H), 1.81 (s, 3H), 1.70 (s, 6H), 0.93 (d, 3H, J=6.4 Hz), 0.88 (d, 3H, J=6.6 Hz).

Provenance & Evidence