Ethyl Acetate → HCID 86613242, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of mesylate 108 (500 mg, 1.26 mmol) in HMPA (2 mL), NaN3 (409 mg, 6.29 mmol) and 15-crown-5 ether (252 mg, 1.26 mmol) were added. The solution was stirred at 55° C. for 3 h. The reaction mixture was added to EtOAc (30 mL), washed with brine (10 mL), dried (Na2SO4) and evaporated. The crude oil was purified by column chromatography (silica gel, EtOAc/Hexanes 1/15) to afford azide 109 (160 mg, 34%) as a colorless oil. Rf 0.33 (AcOEt/Hexanes 1/15). [α]D20=−46.6 (c=0.4, CHCl3). 1H-NMR (500 MHz, CDCl3): 0.04 (s, 6H), 0.88 (s, 9H), 1.32 (d, J=6.7 Hz, 3H), 1.48 (s, 9H), 3.51-3.61 (m, 1H), 4.75-4.90 (m, 2H), 4.50-4.62 (m, 1H). 13C-NMR (125 MHz, CDCl3): −5.5, 14.1, 16.5, 25.8, 28.3, 31.6, 55.2, 57.2, 62.4, 174.3. IR (neat) 3326.1, 2954.0, 2931.1, 2857.9, 2359.9, 2107.2, 1718.2, 1005.7, 1471.2, 1366.0, 1254.5, 1167.7, 1098.0, 838.1.

Provenance & Evidence