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

반응식

[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

참가 물질

반응물 2

HCID 105532-Methyl-2-butene

HCID 663141,2-Epoxy-5-hexene

생성물 1

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

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록: ord-5a6b5ef4906741528eb22f8bdfb25469
출처 데이터셋: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07612106B2

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