1-Pentene → 8-Dodecen-1-ol, (8Z)-

HRID 879040

反応式

HRID 879040 の反応式
[CH2:1]([OH:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[CH2:9].[CH2:11]=[CH:12][CH2:13]CC>C1COCC1>[CH2:1]([OH:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH2:11][CH2:12][CH3:13]

参加物

4

反応物 2

HCID 80041-PenteneHCID 11094728Non-8-en-1-ol

生成物 1

HCID 52832958-Dodecen-1-ol, (8Z)-収率 73%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

In a glovebox, a 20 mL vial was charged with 8-nonenol (0.58 g, 4.1 mmol), 1-pentene (4 mL), and THF (4 mL). A solution of 1 (0.026 g, 1 mol %) in THF (0.5 mL) was added, and the mixture was stirred in an open vial for 4 hours. The vial was removed from the glovebox, the reaction was quenched with excess ethyl vinyl ether, and the solvent was removed in vacuo. Flash chromatography of the residue (SiO2, using a gradient of hexanes to 20% EtOAc in hexanes) provided 12 (0.56 g, 73% yield, 86% Z as determined by 1H-NMR) as a colorless oil; 1H NMR (CDCl3): δ 5.36 (2H, m), 3.64 (2H, br t, J=5.3 Hz), 2.01 (4H, m), 1.36 (2H, m), 1.28-1.40 (11H, m), 0.90 (3H, t, J=7.4 Hz); 13C NMR (CDCl3): δ 130.0, 129.7, 63.1, 32.8, 29.3 (4C), 27.2, 25.7, 22.9, 13.8; HRMS (EI): 184.1805, [C12H24O]+ requires 184.1827.

後処理

  1. customThe vial was removed from the glovebox
  2. customthe reaction was quenched with excess ethyl vinyl ether
  3. customthe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-3a71b7006f57472caad31a2fb3821c47
出典データセット
uspto-grants-2015_03
特許番号
US08987531B2

関連ノート

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