Water → 3-(2-Pyrazinyloxy)-benzaldehyde dimethyl acetal

HRID 1275832ノート

反応式

HRID 1275832 の反応式
[CH3:1][O:2][CH:3]([O:11][CH3:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[CH:5]=1.CC(C)([O-])C.[K+].Cl[C:20]1[CH:25]=[N:24][CH:23]=[CH:22][N:21]=1.O>CN(C)C=O>[CH3:1][O:2][CH:3]([O:11][CH3:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:20]2[CH:25]=[N:24][CH:23]=[CH:22][N:21]=2)[CH:5]=1

参加物

6

反応物 4

HCID 962WaterHCID 73277ChloropyrazineHCID 11275229Phenol, 3-(dimethoxymethyl)-HCID 23665647Potassium tert-butoxide

生成物 1

HCID 221178163-(2-Pyrazinyloxy)-benzaldehyde dimethyl acetal

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A solution of 168 mg of 3-hydroxybenzaldehyde dimethyl acetal in 10 ml of anyhydrous dimethylformamide was stirred under nitrogen and 220 mg of potassium tert-butoxide were added. The mixture was heated at 60° C. for 1 hour, then cooled to room temperature and 115 mg of 2-chloropyrazine were added in portions. The mixture was then heated at 160° C. for 18 hours. After cooling 15 ml of water were added and the product was extracted with 50 ml of ethyl acetate. The extract was washed with 25 ml of 1M sodium hydroxide solution and 25 ml of brine and then dried over anhydrous magnesium sulphate. After filtration and evaporation of the filtrate the residual yellow oil was purified by column chromatography on silica gel using ethyl acetate/hexane (1:1) for the elution to give 3-(2-pyrazinyloxy)-benzaldehyde dimethyl acetal as a yellow oil.

後処理

  1. temperaturecooled to room temperature
  2. temperatureThe mixture was then heated at 160° C. for 18 hours
  3. additionwere added
  4. extractionthe product was extracted with 50 ml of ethyl acetate
  5. washThe extract was washed with 25 ml of 1M sodium hydroxide solution and 25 ml of brine
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationAfter filtration and evaporation of the filtrate the residual yellow oil
  8. customwas purified by column chromatography on silica gel
  9. washfor the elution

出典と根拠

ORDレコード
ord-fc7066c99574438fa6396086fbfe15dd
出典データセット
uspto-grants-2000_12
特許番号
US06162918

反応ノート

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