2,3-Dimethoxyphenol → (E)-3-(2,3-dimethoxy-phenoxy)-but-2-enoic acid ethyl ester

HRID 19225

反応式

HRID 19225 の反応式
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[OH:17].[CH2:18]([O:20][C:21](=[O:26])[CH:22]=[C:23](Cl)[CH3:24])[CH3:19]>O1CCCC1>[CH2:18]([O:20][C:21](=[O:26])/[CH:22]=[C:23](/[O:17][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]([O:15][CH3:16])[C:9]=1[O:8][CH3:7])\[CH3:24])[CH3:19]

参加物

5

反応物 3

HCID 788282,3-DimethoxyphenolHCID 2828353-Chloro-but-2-enoic acid ethyl esterHCID 23665647Potassium tert-butoxide

生成物 1

HCID 66895437(E)-3-(2,3-dimethoxy-phenoxy)-but-2-enoic acid ethyl ester収率 47%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
23 °C

実験手順

Potassium t-butoxide (7.54 g, 0.067 mol) was added to a stirred solution of 2,3-dimethoxy-phenol (5.20 g, 0.034 mol) in tetrahydrofuran (30 mL) at 23° C. under nitrogen and the reaction mixture was heated to reflux for 0.75 h. The reaction mixture was cooled to 23° C. and a solution of 3-chloro-but-2-enoic acid ethyl ester (prepared as in Example 191, 5.00 g, 0.034 mol) in tetrahydrofuran (40 mL) was added to the reaction mixture. The reaction mixture was refluxed for an additional 3 h. After this time, the mixture was concentrated in vacuo and the residue was diluted with water and extracted with diethyl ether. The organic layer was then washed with 5% aqueous sodium hydroxide solution followed by a saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated in vacuo to afford (E)-3-(2,3-dimethoxy-phenoxy)-but-2-enoic acid ethyl ester (4.20 g, 47%) as a yellow oil.

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 0.75 h
  3. temperatureThe reaction mixture was refluxed for an additional 3 h
  4. concentrationAfter this time, the mixture was concentrated in vacuo
  5. additionthe residue was diluted with water
  6. extractionextracted with diethyl ether
  7. washThe organic layer was then washed with 5% aqueous sodium hydroxide solution
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-911a71a02b1849ef91df45cb4bc01a19
出典データセット
uspto-grants-2010_06
特許番号
US07741327B2

関連ノート

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