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

HRID 1275834ノート

反応式

HRID 1275834 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[N:25]=[CH: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[N:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH:5]=1

参加物

6

反応物 4

HCID 962WaterHCID 744042-ChloropyrimidineHCID 11275229Phenol, 3-(dimethoxymethyl)-HCID 23665647Potassium tert-butoxide

生成物 1

HCID 221178593-(2-Pyrimidinyloxy)-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 2 ml of anhydrous 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 114 mg of 2-chloropyrimidine were added in portions. The mixture was heated at 150° C. for 20 hours. After cooling 20 ml of water were added and the product was extracted with ethyl acetate. The extracts were washed with 10 ml of 1M sodium hydroxide solution and 5 ml of brine and then dried over anhydrous magnesium sulphate. After filtration and evaporation of the filtrate the residual brown gum was purified by column chromatography on silica gel using ethyl acetate/hexane (1:1) for the elution to give 3-(2-pyrimidinyloxy)-benzaldehyde dimethyl acetal as a syrup.

後処理

  1. temperaturecooled to room temperature
  2. temperatureThe mixture was heated at 150° C. for 20 hours
  3. additionwere added
  4. extractionthe product was extracted with ethyl acetate
  5. washThe extracts were washed with 10 ml of 1M sodium hydroxide solution and 5 ml of brine
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationAfter filtration and evaporation of the filtrate the residual brown gum
  8. customwas purified by column chromatography on silica gel
  9. washfor the elution

出典と根拠

ORDレコード
ord-c7881455954043e4b313c398881f8d46
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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