Lithium Hydroxide → 3-Methyl-5-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid

HRID 1517054

반응식

HRID 1517054 반응식
C[O:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[CH:7][N:6]=1)=[O:4].[OH-].[Li+]>C1COCC1.CO>[CH3:11][C:10]1[C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:19])([F:20])[F:21])[CH:13]=2)[CH:9]=1

참가 물질

4

반응물 2

HCID 3939Lithium HydroxideHCID 574411233-Methyl-5-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid methyl ester

생성물 1

HCID 574411243-Methyl-5-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid수율 99%

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

실험 절차

To a solution of 1.00 g (3.4 mmol) of 3-methyl-5-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid methyl ester in 40 ml of THF/MeOH (1:1) was added 8.47 ml (8.5 mmol) of lithium hydroxide solution (1 molar in water) and the reaction mixture was stirred at RT. After 20 hours, the solvents were evaporated and the residue poured into crashed ice, the pH was adjusted to 1-2 with HCl 1N and the reaction mixture was extracted twice with EtOAc; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by re-crystallization from CH2Cl2/heptane to give 0.94 g (99%) of the title compound as colorless solid. MS: 280.0 (M−H−).

후처리

  1. customthe solvents were evaporated
  2. additionthe residue poured
  3. extractionthe reaction mixture was extracted twice with EtOAc
  4. washthe organic phases were washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by re-crystallization from CH2Cl2/heptane

출처 및 근거

ORD 기록
ord-d5d0591041db4d76ac2e9f3e13881aed
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08227613B2

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