Methyl iodide → HCID 70268973, compound

Participants

Reaction Conditions

Reaction Steps

A 1.0M solution of lithium bis(trimethylsilyl)amide in THF (2.02 mL, 2.02 mmol) was added to a stirred solution of the ester from Example 110, Step A (400 mg, 1.83 mmol) in THF (8 ml) at -78° C. The solution was stirred at -78° C. for 10 min. Methyl iodide (120 μL, 1.93 mmol) was added. The solution was allowed to warm slowly to RT over 12 h. Saturated NH4Cl solution was added and the mixture extracted with diethyl ether (3×). The combined organic phase was washed with water (2×), brine, dried (MgSO4) and the solvent removed in vacuo. Flash chromatography (silica, 2-3% ethyl acetate-hexanes) afforded the title compound (234 mg, 55%) as a colorless liquid: 1H NMR (400 MHz, CDCl3) δ 7.56 (d, J=8.1 Hz, 2H), 7.40 (d, J=8.3 Hz, 2H), 3.77 (q, J=7.1 Hz, 1H), 3.66 (s, 3H), 1.50 (d, J=7.1 Hz, 3H).

Provenance & Evidence