Methyl iodide → HCID 71269001, compound

Participants

Reaction Steps

To a solution of 8 (50 mg, 0.11 mmol) in THF (3 mL) at −10° C. was slowly added NaH (5.2 mg, 0.12 mmol). The mixture was warmed to rt and stirred for 1 h. To it was added CH3I (50 mg, 0.33 mmol). The reaction mixture was stirred at rt for 16 h, diluted with H2O (10 mL) and extracted with EA (2×20 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by Prep-TLC to give 9 (50 mg, 96% yield) as a white solid. 1H-NMR (400 MHz, CDCl3) δ 9.14-9.11 (m, 1H), 8.24-8.19 (m, 2H), 7.92 (d, J=8.0 Hz, 1H), 7.59-7.54 (m, 1H), 7.44-7.36 (m, 3H), 7.22-7.13 (m, 5H), 7.08-7.04 (m, 1H), 6.72 (d, J=7.2 Hz, 1H), 5.80-5.76 (m, 1H), 5.43-5.30 (m, 2H), 4.20 (d, J=16.8 Hz, 1H), 3.46-3.30 (m, 2H), 3.06-3.00 (m, 1H), 2.75 (s, 3H); MS (ESI+) m/z: 472 [M+H]+.

Provenance & Evidence