Dichloromethane → Propanoic acid, 2-(4-((7-chloro-2-quinoxalinyl)oxy)phenoxy)-, methyl ester

HRID 1939169노트

반응식

HRID 1939169 반응식
Cl[C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][C:6]([Cl:12])=[CH:7][CH:8]=2)[N:3]=1.[OH:13][C:14]1[CH:26]=[CH:25][C:17]([O:18][CH:19]([CH3:24])[C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>CC(C)=O.C(OCC)C.O>[Cl:12][C:6]1[CH:5]=[C:4]2[C:9]([N:10]=[CH:11][C:2]([O:13][C:14]3[CH:15]=[CH:16][C:17]([O:18][CH:19]([CH3:24])[C:20]([O:22][CH3:23])=[O:21])=[CH:25][CH:26]=3)=[N:3]2)=[CH:8][CH:7]=1

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 366926Propanoic acid, 2-(4-hydroxyphenoxy)-, methyl esterHCID 27582232,7-Dichloroquinoxaline

생성물 1

HCID 157156Propanoic acid, 2-(4-((7-chloro-2-quinoxalinyl)oxy)phenoxy)-, methyl ester수율 55.3%

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매HCID 3283Diethyl Ether용매

실험 절차

A mixture of 2,7-dichloroquinoxaline (2.8 g, 14.1 mmol), methyl 2-(4-hydroxyphenoxy)propanoate (2.76 g, 14.1 mmol), and pulverized potassium carbonate (3.9 g, 28.2 mmol) in acetone (70 mL) was refluxed for 3 hours. The reaction mixture was cooled to room temperature and methylene chloride and water were added to the reaction mixture. The organic phase was removed, and the aqueous phase was extracted with methylene chloride. The combined organic phase was washed with water, dried over potassium carbonate, concentrated, and dried under high vacuum. The product was purified by flash chromatography with 6:1 petroleum ether:ethyl ether to afford the desired product (2.8 g, 55% yield) as a solid: mp 103° C.; MS m/e 359 (M+ +H). Anal. Calcd for C18H15ClN2 O4 : C., 60.26; H, 4.21; N, 7.81; Cl, 9.88. Found: C, 60.44, H, 4.31; N, 7.69, Cl, 9.98.

후처리

  1. temperaturewas refluxed for 3 hours
  2. customThe organic phase was removed
  3. extractionthe aqueous phase was extracted with methylene chloride
  4. washThe combined organic phase was washed with water
  5. dry with materialdried over potassium carbonate
  6. concentrationconcentrated
  7. customdried under high vacuum
  8. customThe product was purified by flash chromatography with 6:1 petroleum ether

출처 및 근거

ORD 기록
ord-930405d530e74310859809df0e211bd8
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05696119

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