Methyl iodide → HCID 50900632, compound

Participants

Reaction Steps

Compound 4 (0.405 g, 1.14 mmol) was dissolved in 4 mL of dimethylformamide (DMF) and added to KH (0.46 g, 3.42 mmol). The mixture was stirred at room temperature for 10 min. To this, MeI (0.4 mL, 5.7 mmol) was added dropwise. The reaction was allowed to stir at room temperature for 30 min. The reaction was then quenched with deionized H2O and extracted 3 times with 15 mL dichloromethane. The organic layers were combined and washed 3 times with 15 mL of H2O, and 3 times with 15 mL of brine. The organic layers were dried with MgSO4, and solvent was removed under reduced pressure to give the desired product as a yellow powder without further purification (0.362 g, 86% yield). 1H NMR (300 MHz, CDCl3) δ 7.63 (1H, dd, J=8.0, 1.7 Hz), 7.36 (1H, ddd, J=8.8, 7.3, 1.8 Hz), 7.29-7.19 (2H, m), 7.12 (1H, dd. J=8.2, 1.7 Hz), 7.07-6.92 (5H, m), 6.88 (1H, ddd, J=8.2, 7.3, 1.2 Hz), 6.81 (1H, dd, J=7.8, 1.2 Hz), 3.32 (3H, s), 3.27 (3H, s); 13C (75 MHz, CDCl3) δ 146.5 (q), 143.5 (q), 142.1 (q), 138.8 (q), 132.7 (t), 131.0 (t), 128.7 (q), 127.6 (t), 126.2 (t), 124.2 (t), 124.1 (t), 123.7 (t), 123.1 (t), 120.4 (t), 118.8 (t), 38.5, 38.1.

Provenance & Evidence