Maleic Anhydride → Dimethyl 5-hydroxy-2-(3-methoxy-3-oxopropyl)pyridine-3,4-dicarboxylate

HRID 2389910

反応式

HRID 2389910 の反応式
C(O[C:4]1[O:8][C:7]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[N:6][CH:5]=1)C.[C:15]1(=O)[O:20][C:18](=[O:19])[CH:17]=C1.C[Si](C=[N+]=[N-])(C)C.[CH2:29]([O:31][CH2:32][CH3:33])C.Cl.C[OH:36]>>[OH:8][C:4]1[C:17]([C:18]([O:20][CH3:15])=[O:19])=[C:33]([C:32]([O:31][CH3:29])=[O:36])[C:7]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[N:6][CH:5]=1

参加物

5

反応物 4

HCID 7923Maleic AnhydrideHCID 21893726Hydrochloride methanolHCID 23159941trimethylsilyldiazomethane Et2OHCID 59179423Methyl 3-(5-ethoxy-1,3-oxazol-2-yl)propanoate

生成物 1

HCID 59179398Dimethyl 5-hydroxy-2-(3-methoxy-3-oxopropyl)pyridine-3,4-dicarboxylate収率 30%

実験手順

A mixture of methyl 3-(5-ethoxy-1,3-oxazol-2-yl)propanoate (7.00 g, 35.1 mmol) and maleic anhydride (3.44 g, 35.1 mmol) was stirred at room temperature for 2 hr, 10% hydrochloric acid-methanol solution (100 mL) was added, and the mixture was heated under reflux for 15 hr. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→70/30). The purified product was dissolved in methanol, 2M trimethylsilyldiazomethane/diethyl ether solution (34 mL, 68 mmol) was added at room temperature, and the mixture was stirred for 30 min. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=25/75→50/50) to give the title compound (3.10 g, yield 30%).

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 hr
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→70/30)
  5. dissolutionThe purified product was dissolved in methanol
  6. stirringthe mixture was stirred for 30 min
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=25/75→50/50)

出典と根拠

ORDレコード
ord-d42a55341dc3431886b22fc9a9422f29
出典データセット
uspto-grants-2012_09
特許番号
US08273761B2

関連ノート

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