1,2-Epoxybutane → 6-Carboxy2'-(2-hydroxy-butoxy)-flavone

HRID 462117

반응식

HRID 462117 반응식
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[O:11][C:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[OH:21])=[CH:9][C:8]2=[O:22])([O:3]C)=[O:2].[O:23]1[CH:25]([CH2:26][CH3:27])[CH2:24]1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>O1CCOCC1>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[O:11][C:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH2:24][CH:25]([OH:23])[CH2:26][CH3:27])=[CH:9][C:8]2=[O:22])([OH:3])=[O:2]

참가 물질

5

반응물 3

HCID 78341,2-EpoxybutaneHCID 66854Benzyltrimethylammonium hydroxideHCID 124078666-Carbomethoxy-2'-hydroxy-flavone

생성물 1

HCID 213250166-Carboxy2'-(2-hydroxy-butoxy)-flavone수율 39.3%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

A mixture consisting of 6-carbomethoxy-2'-hydroxy-flavone (10 g), obtained according to the method described in Example 2, and 1,2-epoxy-butane (6 g) and benzyl-trimethylammonium hydroxide (0.5 ml) in dioxane (40 ml) was kept at reflux temperature for 48 hours. After cooling, dilution with water, and extraction with ethylacetate, the organic phase was washed with potassium carbonate 5% and water. The solution was evaporated to dryness, and the resulting product was treated with the stoichiometric quantity of a solution of potassium hydroxide 1% in ethanol 95% at reflux temperature for an hour. After acidification with acetic acid, concentration under vacuum, dilution with water, filtration and double crystallisation from ethanol, 6-carboxy-2'-(2-hydroxy-butoxy)-flavone (4.7 g) was obtained.

후처리

  1. customobtained
  2. temperatureat reflux temperature for 48 hours
  3. temperatureAfter cooling
  4. extractiondilution with water, and extraction with ethylacetate
  5. washthe organic phase was washed with potassium carbonate 5% and water
  6. customThe solution was evaporated to dryness
  7. additionthe resulting product was treated with the stoichiometric quantity of a solution of potassium hydroxide 1% in ethanol 95%
  8. temperatureat reflux temperature for an hour
  9. concentrationAfter acidification with acetic acid, concentration under vacuum, dilution
  10. filtrationwith water, filtration and double crystallisation from ethanol

출처 및 근거

ORD 기록
ord-03f614814f9e4b16b462ae1a0ab78cd4
출처 데이터셋
uspto-grants-1977_12
특허 번호
US04065467

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