Lithium Hydroxide → 2-Methoxy-4-methyl-6-(3-trifluoromethyl-phenyl)-nicotinic acid

HRID 1692390노트

반응식

HRID 1692390 반응식
C[O:2][C:3](=[O:23])[C:4]1[C:9]([CH3:10])=[CH:8][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)=[N:6][C:5]=1[O:21][CH3:22].[OH-].[Li+].Cl.O>C1COCC1.CO>[CH3:22][O:21][C:5]1[N:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:18])[F:19])[CH:12]=2)[CH:8]=[C:9]([CH3:10])[C:4]=1[C:3]([OH:23])=[O:2]

참가 물질

5

반응물 3

HCID 3939Lithium HydroxideHCID 21885828Hydrate;hydrochlorideHCID 57441128HCID 57441128, 화합물

생성물 1

HCID 574411372-Methoxy-4-methyl-6-(3-trifluoromethyl-phenyl)-nicotinic acid수율 77.1%

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

실험 절차

To a solution of 0.325 g (1.00 mmol) of 2-methoxy-4-methyl-6-(3-trifluoromethyl-phenyl)-nicotinic acid methyl ester in 20 ml of THF/MeOH (1:1) was added 2.50 ml (2.50 mmol) of lithium hydroxide solution (1 molar in water) drop by drop and the reaction mixture was then heated up to reflux. After 8 hours, it was poured into crashed ice and acidified with HCl/H2O (1N) to pH 3.0 and then extracted twice with EtOAc; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 4:1) to give 0.24 g (77%) of the title compound as light yellow solid. MS: 310.0 (M−H−).

후처리

  1. temperaturethe reaction mixture was then heated up
  2. temperatureto reflux
  3. additionit was poured
  4. extractionextracted twice with EtOAc
  5. washthe organic phases were washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 4:1)

출처 및 근거

ORD 기록
ord-7757efeda4534b71866da52c8446d5d9
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153805B2

반응 노트

불러오는 중…