2-Furancarboxylic acid → 5-[(1,3-dioxo-2,3-dihydro-1H-2-isoindolyl)methyl]-2-furoic acid

HRID 397700

반응식

HRID 397700 반응식
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=[O:7].O[CH2:10][N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21]>S(=O)(=O)(O)O>[O:21]=[C:12]1[C:13]2[C:14](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:16])[N:11]1[CH2:10][C:5]1[O:1][C:2]([C:6]([OH:8])=[O:7])=[CH:3][CH:4]=1

참가 물질

4

반응물 2

HCID 69192-Furancarboxylic acidHCID 8354N-(hydroxymethyl)phthalimide

생성물 1

HCID 230007015-[(1,3-dioxo-2,3-dihydro-1H-2-isoindolyl)methyl]-2-furoic acid수율 52.8%

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

실험 절차

2-Furoic acid (10.0 g) was dissolved in cold concentrated sulphuric acid (50 ml). The mixture was then added to N-hydroxy methylphthalimide (12.0 g) and the reaction mixture allowed to stand for 18 hrs at room temperature. The mixture was then poured into ice and the product extracted with dichloromethane, dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was triturated with diethyl ether and recrystallised from methanol to afford 5-[(1,3-dioxo-2,3-dihydro-1H-2-isoindolyl)methyl]-2-furoic acid (9.70 g) as a brown solid.

후처리

  1. additionThe mixture was then poured into ice
  2. extractionthe product extracted with dichloromethane
  3. dry with materialdried over magnesium sulphate
  4. customthe solvent removed under reduced pressure
  5. customThe crude product was triturated with diethyl ether
  6. customrecrystallised from methanol

출처 및 근거

ORD 기록
ord-95eaf846f280435abc9809bec6e71199
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610707B1

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