1-Methylimidazole → (E)-1-(2-(3,7-dimethylocta-2,6-dienyloxy)-2-oxoethyl)-3-methyl-1H-imidazol-3-ium chloride

HRID 922001

反応式

HRID 922001 の反応式
[Cl:1][CH2:2][C:3]([O:5][CH2:6]/[CH:7]=[C:8](\[CH3:15])/[CH2:9][CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])=[O:4].[CH3:16][N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1>C(OCC)C>[Cl-:1].[CH3:15]/[C:8](/[CH2:9][CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])=[CH:7]\[CH2:6][O:5][C:3](=[O:4])[CH2:2][N:19]1[CH:20]=[CH:21][N+:17]([CH3:16])=[CH:18]1

参加物

4

反応物 2

HCID 13901-MethylimidazoleHCID 5890636(E)-3,7-dimethylocta-2,6-dienyl 2-chloroacetate

生成物 1

HCID 86662343(E)-1-(2-(3,7-dimethylocta-2,6-dienyloxy)-2-oxoethyl)-3-methyl-1H-imidazol-3-ium chloride収率 67%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
40 °C

実験手順

Geraniol ester [2] (2.307 g, 10 mmol) and N-methylimidazole (0.821 g, 10 mmol) were mixed in and stirred in a sealed vessel at 40° C. for 24 hrs. A light-brown solid was formed and suspended in anhydrous diethylether. The solid precipitate was filtered, washed with diethylether and dried under reduced pressure (0.01 mbar) to give imidazolium chloride [3] in 67% yield as light-yellow hygroscopic solid. The product was pure according to 1H NMR and directly subjected to the next step without further purification. 1H-NMR (300 MHz, d6-DMSO) δ(ppm)=9.36 (s, 1H), 7.82 (s, 2H), 5.37 (s, 2H), 5.33 (t, J=7.0 Hz, 1H), 5.07 (s, 1H), 4.68 (d, J=7.1 Hz, 2H), 3.93 (s, 3H), 2.03 (m, 4H), 1.66 (s, 3H), 1.64 (s, 3H), 1.56 (s, 3H). 13C-NMR (75 MHz, d6-DMSO) δ(ppm)=166.9, 142.6, 137.8, 131.1, 123.7, 123.6, 123.3, 117.8, 62.4, 49.4, 35.9, 25.8, 25.5, 17.6, 16.1. mp 160° C. (dec), T5%onset 125° C.

後処理

  1. customA light-brown solid was formed
  2. filtrationThe solid precipitate was filtered
  3. washwashed with diethylether
  4. customdried under reduced pressure (0.01 mbar)

出典と根拠

ORDレコード
ord-4884273215d1442da00061d58cc08139
出典データセット
uspto-grants-2016_03
特許番号
US09278134B2

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