Sodium hydride → HCID 54406088、化合物

HRID 2225731ノート

反応式

HRID 2225731 の反応式
[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[H-].[Na+].S([O-])(=O)(=O)C.[N:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([O:31][CH2:32][CH2:33]O)=[CH:23][CH:22]=1>CN(C)C=O.C(O)(=O)C>[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:33][CH2:32][O:31][C:24]2[C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:21]=[CH:22][CH:23]=2)=[CH:7][CH:6]=1

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 85257MethanesulfonateHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl esterHCID 1900450524220-96-0

生成物 1

HCID 54406088HCID 54406088、化合物収率 56.9%

試薬・触媒・溶媒 2

HCID 176Acetic Acid触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (1.267 g) in dimethylformamide (10 mL) under argon was treated with 55% sodium hydride (0.305 g), stirred for 15 minutes and treated with the mesylate prepared from 1.135 g of 2-(4-quinolyloxy)ethanol. The mixture was heated under argon at 60° C. for 3 hours. The cooled mixture was treated with glacial acetic acid (2 drops) and the volatiles were removed under vacuum. The residue was mixed with dichloromethane and dilute cold sodium bicarbonate solution. The dichloromethane extracts were washed with water, dried (Na2SO4), filtered, and evaporated to give crude product. The material was purified by HPLC (ethyl acetate-methanol; 20: 1) and crystallized from dichloromethane-hexane to provide 1.2 g of alpha-oxo-4-[[2-(4-quinolyloxy)ethyl]oxy]benzeneacetic acid methyl ester as a colorless solid, mp 135°-136° C.

後処理

  1. customthe volatiles were removed under vacuum
  2. additionThe residue was mixed with dichloromethane
  3. additiondilute cold sodium bicarbonate solution
  4. washThe dichloromethane extracts were washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto give crude product
  9. customThe material was purified by HPLC (ethyl acetate-methanol; 20: 1)
  10. customcrystallized from dichloromethane-hexane

出典と根拠

ORDレコード
ord-af2feac2dcef4e659eb5c5403ca81ad8
出典データセット
uspto-grants-1994_09
特許番号
US05344843

反応ノート

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