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Sodium hydride → N-[2-(4-phenoxyphenoxy)-ethoxy]-pyrazole

HRID 1681666
ノート
印刷プレビュー

反応式

HRID 1681666 の反応式
[OH:1][N:2]1[CH:6]=[CH:5][CH:4]=[N:3]1.[H-].[Na+].[O:9]([C:16]1[CH:35]=[CH:34][C:19]([O:20][CH2:21][CH2:22]C2C=C(S([O-])(=O)=O)C=CC=2C)=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CN(C)C=O>[O:9]([C:16]1[CH:17]=[CH:18][C:19]([O:20][CH2:21][CH2:22][O:1][N:2]2[CH:6]=[CH:5][CH:4]=[N:3]2)=[CH:34][CH:35]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 30167331-hydroxy-1H-pyrazoleHCID 867441102-[(p-Phenoxyphenoxy)-ethyl]p-toluenesulfonate

生成物 1

HCID 15096501N-[2-(4-phenoxyphenoxy)-ethoxy]-pyrazole収率 76.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

反応条件

温度
0 °C

実験手順

While cooling and at 0° C., a solution of 1.0 g of N-hydroxypyrazole in 10 ml of dimethylformamide is dripped into a suspension of 0.3 g of sodium hydride in 10 ml of dimethylformamide. The mixture is stirred for a further hour, after which a solution of 4.7 g of 2-(4-phenoxyphenoxy)-ethyl-p-toluenesulfonate in 50 liters of dimethylformamide is added. The reaction batch is stirred for 12 hours at room temperature and then poured into 250 ml of ice water. The mixture is extracted three times with methyl tert-butyl ether, and the combined extracts are washed with 1N sodium hydroxide solution and then with water. The organic phase is dried with sodium sulfate, the solvent is stripped off under reduced pressure and the residue is chromatographed over silica gel using toluene as developer; there is obtained 2.7 g of N-[2-(4-phenoxyphenoxy)-ethoxy]-pyrazole of melting point 83°-85° C.

後処理

  1. stirringThe reaction batch is stirred for 12 hours at room temperature
  2. extractionThe mixture is extracted three times with methyl tert-butyl ether
  3. washthe combined extracts are washed with 1N sodium hydroxide solution
  4. dry with materialThe organic phase is dried with sodium sulfate
  5. customthe residue is chromatographed over silica gel

出典と根拠

ORDレコード
ord-38b8791285e74fab9fffdb29c4d6d65e
出典データセット
uspto-grants-1992_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05173501

反応ノート

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