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

HRID 2307523노트

반응식

HRID 2307523 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6342Acetonitrile용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-96b0c7a0bfa341cf9e930b6e154179d3
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06831148B2

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