2-Bromoethyl methyl ether → HCID 178495812, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 183B (240 mg, 0.84 mmol) in N,N-dimethylformamide tetrahydrofuran (1:4, 10 mL) were added a solution of potassium tert-butoxide (Aldrich, 133 mg, 1.2 mmol) and commercially available, 2-bromoethyl methyl ether (Aldrich, 104 μL, 1.2 mmol). The reaction mixture was stirred at 80° C. for 16 hours, cooled to room temperature, quenched with saturated aqueous NaHCO3 (10 mL) and extracted with ethyl acetate (3×10 mL,). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-100% ethyl acetate in hexanes) to afford the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ ppm 1.59-1.77 (m, 6 H), 1.84-1.91 (m, 6 H), 1.95-2.04 (m, 3 H), 3.26 (s, 3 H), 3.71 (t, J=5.3 Hz, 2 H), 4.36 (t, J=5.1 Hz, 2 H), 8.54 (s, 1 H); MS (ESI+) m/z 346 (M+H)+; Anal. Calculated for C18H23N3O2S: C, 62.58; H, 6.71; N, 12.16. Found: C, 62.15; H, 6.89; N, 11.95.

Provenance & Evidence