1-Dodecene → 40642-44-2

HRID 879047ノート

反応式

HRID 879047 の反応式
[CH2:1]([OH:6])[CH2:2][CH2:3][CH:4]=[CH2:5].[CH2:7]=[CH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]CC>C1COCC1>[CH2:1]([OH:6])[CH2:2][CH2:3]/[CH:4]=[CH:5]\[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

参加物

4

反応物 2

HCID 81831-DodeceneHCID 131814-Penten-1-OL

生成物 1

HCID 1100967940642-44-2収率 62%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
35 °C

実験手順

In a glovebox, a 20 mL vial was charged with 4-pentenol (410 μL, 3.98 mmol), 1-dodecene (4.4 mL), and THF (2.7 mL). A solution of 1 (0.025 g, 1 mol %) in THF (0.5 mL) was added, and the mixture was stirred in an open vial for 6 hours at 35° C. 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 8% EtOAc in hexanes) provided 21 (0.56 g, 62% yield, 84% Z as determined by 13C-NMR) as a colorless oil; 1H NMR (CDCl3): δ 5.38 (2H, m), 3.65 (2H, m), 1.95-2.14 (4H, m), 1.63 (2H, m), 1.52 (1H, s), 1.25 (16H, m), 0.87 (3H, t, J=6.9 Hz); 13C NMR (100 Hz, CDCl3): δ 131.0, 128.9, 62.8, 32.8, 32.1, 29.9, 29.8, 29.7 (2C), 29.5 (2C), 29.3, 23.7, 22.8, 14.2; HRMS (FAB): 227.2372, [C15H30O+H]+ requires 227.2369.

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-1e2578ba8a654d739ad19f833216d5c3
出典データセット
uspto-grants-2015_03
特許番号
US08987531B2

反応ノート

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