Sodium Hydroxide → HCID 57910810, compound

Participants

Reaction Steps

Lithium aluminum hydride (7.80 mL of a 1.0 M solution in THF, 7.80 mmol) was added to a stirred solution of 1c (2.46 g, 5.22 mmol) in diethyl ether (10.0 mL) at 0° C. After approximately 10 min, 1N NaOH was added to quench the reaction followed by dilution with EtOAc. The resulting mixture was dried (magnesium sulfate), filtered and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel (gradient elution; 0%-100% EtOAc/hexanes as eluent) to afford the title compound 1d. m/z (ES) 430 (MH)+. 1HNMR (500 MHz, CDCl3): δ 8.61 (d, 1H, J=4.5 Hz), 8.40 (d, 1H, J=2.5 Hz), 7.75 (m, 1H), 7.67 (d, 211, J=8.5 Hz), 7.53 (d, 1H, J=8.0 Hz), 7.47 (d, 2H, J=8.5 Hz), 7.29 (m, 1H), 7.19 (m, 2H), 6.53 (s, 1H), 5.23 (s, 2H), 4.81 (s, 2H), 3.08 (m, 1H), 1.68 (s, 3H), 0.87 (d, 3H, J=6.6 Hz), 0.80 (d, 3H, J=6.9 Hz).

Provenance & Evidence