Triethylamine → Ethyl 4-methyl-3-(pyridin-4-yl)isoxazole-5-carboxylate

HRID 2388195노트

반응식

HRID 2388195 반응식
O[N:2]=[C:3]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)[CH:4]([CH3:12])[C:5](=[O:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7].C(N(CC)CC)C.S(Cl)(C)(=O)=O>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH3:12][C:4]1[C:3]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:2][O:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 136341743Ethyl 4-(hydroxyimino)-3-methyl-2-oxo-4-(pyridin-4-yl)butanoate

생성물 1

HCID 67530753Ethyl 4-methyl-3-(pyridin-4-yl)isoxazole-5-carboxylate수율 117.4%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 516892Sodium Bicarbonate용매

실험 절차

Ethyl 4-(hydroxyimino)-3-methyl-2-oxo-4-(pyridin-4-yl)butanoate (4.68 g, 18.7 mmol) and triethylamine (3.4 mL, 24.3 mmol) were added to 120 mL of CH2Cl2. Mesyl chloride (1.9 mL, 24.3 mmol) was added and the mixture was stirred at room temperature for 20 h. The reaction mixture was diluted with CH2Cl2 and saturated sodium bicarbonate solution was added. The aqueous layer was extracted with additional CH2Cl2 and the combined organic layer was washed with brine and dried over MgSO4. The solvent was removed in vacuo to afford 5.1 g of the title compound. MS: (+) m/z 233.35 (M+1).

후처리

  1. additionwas added
  2. extractionThe aqueous layer was extracted with additional CH2Cl2
  3. washthe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-7c056bbdc96d40ccb101012d47146253
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08269008B2

반응 노트

불러오는 중…