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

HRID 1432798Notes

Reaction equation

HRID 1432798 reaction equation
[CH2:1]([CH:5]1[CH2:7][O:6]1)CC=C.[CH3:8][C:9](=[CH:11][CH3:12])[CH3:10]>>[CH3:8][C:9]([CH3:10])=[CH:11][CH2:12][CH2:1][CH:5]1[CH2:7][O:6]1

Participants

3

Reactant 2

HCID 105532-Methyl-2-buteneHCID 663141,2-Epoxy-5-hexene

Product 1

HCID 134343712-(4-Methylpent-3-enyl)oxirane

Procedure

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).

Workup

  1. customSolvent was removed under reduced pressure
  2. customthe residue purified by column chromatography (0-10% EtOAc/n-hexane/silica)

Sources & evidence

ORD record
ord-5a6b5ef4906741528eb22f8bdfb25469
Source dataset
uspto-grants-2009_11
Patent number
US07612106B2

Reaction notes

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