2-Methyl-2-butene → 2-(4-Methylpent-3-enyl)oxirane

Participants

Reaction Steps

2-(But-3-enyl)oxirane (1.000 g, 10 mmol) and 2-methylbut-2-ene (10 g, 102 mmol) were stirred at room temperature for 24 hr in a sealed scintillation vial with Zhan catalyst 1 (0.057 g, 0.086 mmol). Solvent was removed under reduced pressure and the residue purified by column chromatography (0-10% EtOAc/n-hexane/silica) to give 2-(4-methylpent-3-enyl)oxirane as a colorless oil. 1H NMR (CDCl3): δ 5.2-5.1 (m, 1H), 2.95-2.88 (m, 1H), 2.75 (dd, 1H J1=5.0, J2=4.1), 2.48 (dd, 1H J1=5.0, J2=2.8), 2.15 (2H, q, J=7.4), 1.70 (s, 3H), 1.63 (s, 3H), 1.60-1.50 (m, 2H).

Provenance & Evidence