Triethylamine → 2-(5-Formyl-isoxazol-3-yl)-pyridine

HRID 2407708ノート

反応式

HRID 2407708 の反応式
N1C=CC=CC=1.S(=O)(=O)=O.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:21]=[C:20]([CH2:22][OH:23])[O:19][N:18]=1.C(N(CC)CC)C>CS(C)=O.ClCCl.C(OCC)(=O)C>[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:21]=[C:20]([CH:22]=[O:23])[O:19][N:18]=1

参加物

7

反応物 3

HCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 6865423-(2-Pyridinyl)-5-isoxazolemethanol

生成物 1

HCID 226312282-(5-Formyl-isoxazol-3-yl)-pyridine収率 18%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Sulfur trioxide pyridine (10.0 g, 62.8 mmol) was dissolved in dimethylsulfoxide (50 mL) and cooled to near 0° C. A solution of the compound prepared in Example 124 (5.05 g, 28.7 mmol) and triethylamine (16.0 mL, 115 mmol) in dichloromethane (40 mL) was added to the solution over 45 minutes. The reaction was warmed to room temperature and stirred overnight. The reaction was diluted with ethyl acetate and washed with sodium hydrogen carbonate aqueous solution. The organic phase was washed with water and dried over magnesium sulfate. The crude mixture was purified by column chromatography using an eluant of 1 to 3% ethyl acetate/dichloromethane to provide the title compound (0.90 g) with the following physical data.

後処理

  1. temperaturecooled
  2. customto near 0° C
  3. washwashed with sodium hydrogen carbonate aqueous solution
  4. washThe organic phase was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customThe crude mixture was purified by column chromatography

出典と根拠

ORDレコード
ord-13a27517018148cda4c13d12c0b4ee0e
出典データセット
uspto-grants-2014_08
特許番号
US08809538B2

反応ノート

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