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

HRID 2407708노트

반응식

HRID 2407708 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-13a27517018148cda4c13d12c0b4ee0e
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08809538B2

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