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

HRID 1939169

反応式

HRID 1939169 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-930405d530e74310859809df0e211bd8
出典データセット
uspto-grants-1997_12
特許番号
US05696119

関連ノート

読み込み中…