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

HRID 274216

반응식

HRID 274216 반응식
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

참가 물질

6

반응물 4

HCID 8028Tetrahydrofuran2회HCID 25517Ammonium ChlorideHCID 69688Furo[3,4-b]pyridine-5,7-dioneHCID 178491912HCID 178491912, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b52f5b32182147ada5b88506affe7b8f
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05389620

연결된 노트

불러오는 중…