1-Hexene → (+/-)-(E)-2-(oct-3-enyl)oxirane

HRID 1295074

反応式

HRID 1295074 の反応式
[CH2:1]([CH:5]1[CH2:7][O:6]1)[CH2:2][CH:3]=[CH2:4].[CH2:8]=[CH:9][CH2:10][CH2:11]CC>>[CH2:1]([CH:5]1[CH2:7][O:6]1)[CH2:2]/[CH:3]=[CH:4]/[CH2:8][CH2:9][CH2:10][CH3:11]

参加物

3

反応物 2

HCID 115971-HexeneHCID 663141,2-Epoxy-5-hexene

生成物 1

HCID 58906870(+/-)-(E)-2-(oct-3-enyl)oxirane

実験手順

2-(But-3-enyl)oxirane (1.000 g, 10.2 mmol) and hex-1-ene (9.12 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 (±)-(E)-2-(oct-3-enyl)oxirane as a colorless oil. 1H NMR (CDCl3): δ 5.5–5.4 (m, 2H), 3.0–2.9 (m, 1H), 2.8–2.7 (m, 1H), 2.5–2.45 (m, 1H), 2.2–2.1 (m, 2H), 1.99 (q, 2H, J=5.7), 1.65–1.55 (m, 2H), 1.35–1.25 (m, 4H), 0.95–0.85 (m, 3H). Contains ca 20% (Z)-2-(oct-3-enyl)oxirane.

後処理

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

出典と根拠

ORDレコード
ord-d2a8983549644bd1955bff69460498b3
出典データセット
uspto-grants-2007_07
特許番号
US07241792B2

関連ノート

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