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

HRID 397700

反応式

HRID 397700 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-95eaf846f280435abc9809bec6e71199
出典データセット
uspto-grants-2003_08
特許番号
US06610707B1

関連ノート

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