6-Chloro-1-hexanol → (E)-4-butoxy-3-methoxycinnamic acid 6-hydroxyhexyl ester

HRID 2307523ノート

反応式

HRID 2307523 の反応式
[CH2:1]([O:5][C:6]1[CH:16]=[CH:15][C:9](/[CH:10]=[CH:11]/[C:12]([OH:14])=[O:13])=[CH:8][C:7]=1[O:17][CH3:18])[CH2:2][CH2:3][CH3:4].Cl[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26]>C(#N)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[OH:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][O:13][C:12](=[O:14])/[CH:11]=[CH:10]/[C:9]1[CH:15]=[CH:16][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[C:7]([O:17][CH3:18])[CH:8]=1

参加物

5

反応物 2

HCID 748286-Chloro-1-hexanolHCID 59335643-(4-Butoxy-3-methoxyphenyl)prop-2-enoic acid

生成物 1

HCID 20744698(E)-4-butoxy-3-methoxycinnamic acid 6-hydroxyhexyl ester収率 79.3%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6342Acetonitrile溶媒2 回

実験手順

1.38 g (5.50 mmol) (E)-4-butyloxy-3-methoxycinnamic acid was suspended in 3 ml acetonitrile. A mixture of 0.84 g (5.50 mmol) 1,8-diazabicyclo[5 4.0]undec-7-ene(1,5-5) (DBU) and 3 ml acetonitrile was added dropwise over a period of 5 minutes. 0.46 g (1.25 mmol) tetrabutylammonium iodide and 0.68 g (5.00 mmol) 6-chlorohexanol was added and the resulting mixture was then refluxed for 6 hours. The reaction mixture was cooled and then extracted using ethyl acetate and water. The ethyl acetate phase was washed with water, dried over sodium sulfate, filtered and concentrated by rotary evaporation. The residue was purified by chromatography using a silica gel column (120 g) and toluene:ethyl acetate (1:1) as eluant to give 1.39 g (79%) (E)-4-butyloxy-3-methoxycinnamic acid 6-hydroxyhexyl ester as colourless oil.

後処理

  1. additionwas added dropwise over a period of 5 minutes
  2. temperaturethe resulting mixture was then refluxed for 6 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted
  5. washThe ethyl acetate phase was washed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation
  9. customThe residue was purified by chromatography

出典と根拠

ORDレコード
ord-96b0c7a0bfa341cf9e930b6e154179d3
出典データセット
uspto-grants-2004_12
特許番号
US06831148B2

反応ノート

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