Furo[3,4-b]pyridine-5,7-dione → 2-(2-Benzyloxy-4-methoxyphenylcarbonyl)-3-pyridine carboxylic acid

HRID 274217

反応式

HRID 274217 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[C:7]([O:9][C:10](=[O:11])[C:2]=12)=[O:8].[CH2:12]([O:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=1[Li])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(OC1C=C(OC)C=CC=1Br)C1C=CC=CC=1.[Li]CCCC>C1COCC1>[CH2:12]([O:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=1[C:10]([C:2]1[C:3]([C:7]([OH:9])=[O:8])=[CH:4][CH:5]=[CH:6][N:1]=1)=[O:11])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

6

反応物 4

HCID 69688Furo[3,4-b]pyridine-5,7-dioneHCID 184340291-Bromo-4-methoxy-2-phenylmethoxybenzeneHCID 178418339ButyllithiumHCID 178506736HCID 178506736、化合物

生成物 1

HCID 152284862-(2-Benzyloxy-4-methoxyphenylcarbonyl)-3-pyridine carboxylic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a THF (20 ml) solution of pyridine-2,3-dicarboxylic acid anhydride (1.92 g, 12.9 mmol) was added a THF solution of 2-benzyloxy-4-methoxyphenyllithium (10 ml), which was prepared from 2-benzyloxy-4-methoxyphenyl bromide (3.77 g, 12.9 mmol) and BuLi (1.6M hexane solution, 8.85 ml, 14.2 mmol) at -78° C., at -78° C. over a period of 5 min. The temperature of the mixture was raised to room temperature and the mixture was additionally stirred at the same temperature for 2 h. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between 1N HCl and AcOEt. The organic layer was washed with 1N HCl dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was dissolved in 1N NaOH and the solution was washed with AcOEt and chloroform. The aqueous layer was acidified with conc. HCl and extracted with AcOEt. The organic layer was washed with 1N HCl and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residual solid was recrystallized from is chloroform-ether to give 2-(2-benzyloxy-4-methoxyphenylcarbonyl)-3-pyridine carboxylic acid (2,03 g) as a colorless solid.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between 1N HCl and AcOEt
  3. washThe organic layer was washed with 1N HCl
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in 1N NaOH
  8. washthe solution was washed with AcOEt and chloroform
  9. extractionextracted with AcOEt
  10. washThe organic layer was washed with 1N HCl and brine
  11. dry with materialdried over Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure
  14. customThe residual solid was recrystallized

出典と根拠

ORDレコード
ord-367bd30b300149b1b99a120d3f2e679d
出典データセット
uspto-grants-1995_02
特許番号
US05389620

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