Ethyl Bromide → HCID 90411361, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of the product of Example 1, step (g) (0.068 g, 0.26 mmol) in DMF (4 ml) at 0° C. under argon was added NaH (60% dispersion by wt., 0.015 g, 0.39 mmol) followed by ethyl bromide (0.029 ml, 0.39 mmol). The reaction mixture was stirred at 0° C. for 2 hrs and then quenched by slow addition of saturated aqueous citric acid (40 ml). The aqueous mixture was extracted with DCM (3×). The combined DCM extracts were washed with water (2×), brine, dried (MgSO4), filtered, and solvent evaporated in vacuo to give the crude product. Purification by silica-gel chromatography (gradient elution: 0 to 50% EtOAc in hexanes) gave the sub-titled compound as a tan solid (0.060 g). 1H NMR (CDCl3) δ 6.75 (d, J=3.0 Hz, 1 H), 6.24 (d, J=3.0 Hz, 1H), 4.40-4.08 (m, 4H), 3.96-3.62 (m, 4 H), 3.34-2.92 (m, 4 H), 1.42 (t, J=6.9 Hz, 3 H), 1.28 (t, J=6.9 Hz, 3H); MS: ESI (positive): 293 (M+H).

Provenance & Evidence