Methanol → [2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-acetic Acid Methyl Ester

HRID 890448노트

반응식

HRID 890448 반응식
[CH3:1][C:2]1[C:7]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:5]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[N:3]=1.S(Cl)(Cl)=O.[CH3:26]O>>[CH3:26][O:10][C:9](=[O:11])[CH2:8][C:7]1[C:2]([CH3:1])=[N:3][C:4]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:21])[F:20])=[CH:14][CH:13]=2)=[CH:5][CH:6]=1

참가 물질

4

반응물 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 21935927[2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-acetic Acid

생성물 1

HCID 67072318[2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-acetic Acid Methyl Ester수율 97.3%

실험 절차

A solution of 2.55 g (8.63 mmol) of [2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-acetic acid in 25 ml of methanol was cooled to −10° C.; 1.88 ml (25.9 mmol) of thionyl chloride were added. The reaction mixture was then stirred at ambient temperature for 2 hours. Subsequently, the solution was stirred with ice water, then extracted with three portions of 50 ml of tert.-butyl methyl ether. The combined organic layers were washed with water, aqueous sodium hydrogen carbonate, brine and dried on anhydrous sodium sulfate. After evaporation of the solvent, 2.6 g (97.3%) of the title compound were obtained as light brown solid.

후처리

  1. extractionextracted with three portions of 50 ml of tert.-butyl methyl ether
  2. washThe combined organic layers were washed with water, aqueous sodium hydrogen carbonate, brine
  3. dry with materialdried on anhydrous sodium sulfate
  4. customAfter evaporation of the solvent

출처 및 근거

ORD 기록
ord-a00a7dc5dcf94b038d325c9c2737aac9
출처 데이터셋
uspto-grants-2006_02
특허 번호
US06995263B2

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