HCID 57910785, compound → HCID 24758850, compound

Participants

Reaction Steps

Methyl magnesium bromide (30.9 mL of a 1.4 M solution in THF:toluene (25:75)) was added to a stirred solution of 7c (14.0 g, 30.9 mmol) in a mixture of THF (130 mL) and diethyl ether (260 mL) at 0° C. After approximately 1 h at 0° C., the reaction was quenched by the addition of saturated aqueous ammonium chloride, and the resulting mixture stirred for 15 min. The organic phase was separated, and the aqueous phase was 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; 0%-100% acetone/DCM as eluent) to furnish the title compound 7d. m/z (ES) 470 (MH)+. 1HNMR (500 MHz, CDCl3): δ 9.01 (d, 1H, J=9.1 Hz), 8.88 (d, 2H, J=5.0 Hz), 8.73 (d, 1H, J=9.2 Hz), 8.52 (d, 1H, J=2.7 Hz), 8.34 (dd, 1H, J=3.0, 9.4 Hz), 8.25 (d, 2H, J=8.5 Hz), 8.17 (d, 1H, J=9.1 Hz), 7.65 (d, 2H, J=8.5 Hz), 7.53 (t, 1H, J=5.0 Hz), 5.62 (s, 2H), 3.05 (m, 1H, J=6.7 Hz), 1.91 (s, 3H), 1.75 (s, 6H), 1.00 (d, 3H, J=6.6 Hz), 0.96 (d, 3H, J=6.4 Hz).

Provenance & Evidence