Tetrahydrofuran → 3-Pyridinecarboxylic acid, 2-(4-methoxybenzoyl)-

HRID 274216

反応式

HRID 274216 の反応式
C1COCC1.[N:6]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:12]([O:14][C:15](=[O:16])[C:7]=12)=[O:13].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([Mg]Br)=[CH:21][CH:20]=1.[NH4+].[Cl-]>Cl>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:15]([C:7]2[C:8]([C:12]([OH:14])=[O:13])=[CH:9][CH:10]=[CH:11][N:6]=2)=[O:16])=[CH:21][CH:20]=1

参加物

6

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 25517Ammonium ChlorideHCID 69688Furo[3,4-b]pyridine-5,7-dioneHCID 178491912HCID 178491912、化合物

生成物 1

HCID 113343683-Pyridinecarboxylic acid, 2-(4-methoxybenzoyl)-収率 27.8%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

To a THF (15 ml) solution of pyridine-2,3-dicarboxylic acid anhydride (1.0 g, 6.7 mmol) was added dropwise a THF solution of 4-methoxyphenylmagnesium bromide (0.89M, 8.0 ml, 7.1 mmol) at -78° C. The reaction mixture was stirred at the same temperature for 1 h and then a saturated aqueous solution of NH4Cl (20 ml) was added to quench the reaction. The reaction mixture was diluted with 1N HCl and extracted with AcOEt. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (E. Merck, Kieselgel 60/chloroform:methanol=10:1) to give 2-(4-methoxyphenylcarbonyl)-3-pyridine carboxylic acid (479 mg) as a colorless solid.

後処理

  1. customto quench
  2. customthe reaction
  3. extractionextracted with AcOEt
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (E. Merck, Kieselgel 60/chloroform:methanol=10:1)

出典と根拠

ORDレコード
ord-b52f5b32182147ada5b88506affe7b8f
出典データセット
uspto-grants-1995_02
特許番号
US05389620

関連ノート

読み込み中…