Sodium hydride → HCID 15390573、化合物

HRID 1740814ノート

反応式

HRID 1740814 の反応式
[H-].[Na+].[N:3]1([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[N:4]1.C1(C)C=CC(S(O[CH2:26][CH2:27][O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)(=O)=O)=CC=1>CN(C)C=O>[N:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[O:28][CH2:27][CH2:26][O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][N:3]2[CH:7]=[CH:6][CH:5]=[N:4]2)=[CH:10][CH:11]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 1334121-(4-Hydroxybenzyl)pyrazoleHCID 14480093HCID 14480093、化合物

生成物 1

HCID 15390573HCID 15390573、化合物収率 40.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

To a mixture of 10 ml of anhydrous N,N-dimethylformamide and 72 mg of sodium hydride (60% oil dispersion) was added dropwise an anhydrous N,N-dimethyl-formamide (5 ml) solution of 300 mg of 4-(1-pyrazolyl)methylphenol under stirring over 10 minutes. After stirring at room temperature for 1 hour, the mixture was cooled to 5° to 10° C., to which an anhydrous N,N-dimethylformamide (5 ml) solution of 505 mg of 2-(2-pyridyloxy)ethyl p-toluenesulfonate was added dropwise over 30 minutes. The mixture was stirred at room temperature overnight and then at 60° to 70° C. for further 2 hours. The reaction mixture was poured into 50 ml of ice water, which was extracted twice with 30 ml of ethyl acetate. The organic layers were combined, washed with water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, which afforded 208 mg of 4-(1-pyrazolyl)methylphenyl 2-(2-pyridyloxy)ethyl ether (compound 1). Yield, 41%.

後処理

  1. stirringAfter stirring at room temperature for 1 hour
  2. additionwas added dropwise over 30 minutes
  3. stirringThe mixture was stirred at room temperature overnight
  4. waitat 60° to 70° C. for further 2 hours
  5. extractionwas extracted twice with 30 ml of ethyl acetate
  6. washwashed with water
  7. dry with materialdried with anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-7af913a8daf742ceb87cbaf2bdcddd70
出典データセット
uspto-grants-1999_10
特許番号
US05972949

反応ノート

読み込み中…