Sodium hydride → HCID 86607686, compound

To a solution of 7-Cyclopropyl-hept-5-ene-1,2-diol (1.45 g, 9.28 mmol) in THF (30 mL) was added 60% sodium hydride (1.1 g, 27.84 mmol) at 0° C. The mixture was slowly warmed to room temperature and stirred for 1 h. TrisIm (3.41 g, 10.2 mmol) was added in one portion at 0° C. followed stirring at room temperature for 1.5 h. The mixture was quenched with water and extracted with Et2O. The organics were washed with brine, dried over MgSO4, filtered, and concentrated. Purification by silica gel chromatography (7% EtOAc in hexanes gradient to 14% EtOAc in hexanes) gave 2-(4-Cyclopropyl-but-2-enyl)-oxirane as a clear oil; 1H NMR (400 MHz, CDCl3): δ 5.54–5.48 (m, 1H), 5.44–5.37 (m, 1H), 2.94–2.91 (m, 1H), 2.75 (dd, 1H, J1=4.9 Hz, J2=4.1 Hz), 2.48 (dd, 1H, J1=5.0 Hz, J2=2.7 Hz), 2.19 (q, 2H, J=7.3 Hz), 1.98 (t, 2H, J=7.0 Hz), 1.62–1.56 (m, 2H), 0.75–0.66 (m, 1H), 0.44–0.39 (m, 2H), 0.09–0.05(m, 2H).