Potassium Iodide → 7-benzyloxy-6-D-glucosyloxycoumarin

HRID 2689

反応式

HRID 2689 の反応式
[CH:1]1[C:6]([O:7][C@@H:8]2[O:13][C@H:12]([CH2:14][OH:15])[C@@H:11]([OH:16])[C@H:10]([OH:17])[C@H:9]2[OH:18])=[C:5]([OH:19])[CH:4]=[C:3]2[O:20][C:21]([CH:23]=[CH:24][C:2]=12)=[O:22].[CH2:25](Cl)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.[I-].[K+]>CN(C)C=O>[CH2:25]([O:19][C:5]1[CH:4]=[C:3]2[C:2]([CH:24]=[CH:23][C:21](=[O:22])[O:20]2)=[CH:1][C:6]=1[O:7][CH:8]1[O:13][C@H:12]([CH2:14][OH:15])[C@@H:11]([OH:16])[C@H:10]([OH:17])[C@H:9]1[OH:18])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

参加物

7

反応物 5

HCID 4875Potassium IodideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 5281417Esculin

生成物 1

HCID 228840427-benzyloxy-6-D-glucosyloxycoumarin収率 86.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

Esculin (1.0 g), benzyl chloride (1.0 g), potassium carbonate (0.7 g), catalytic amounts of 18-crown-6-ether and potassium iodide, and dimethylformamide (40 ml) were placed in an eggplant-shaped flask (100 ml). The mixture was reacted while stirred at 60° C. for 8 hours. The reaction mixture was concentrated under reduced pressure and the residue was poured into ice water. The precipitated crystals were filtered out and recrystallized from methanol to obtain 7-benzyloxy-6-D-glucopyranosyloxycoumarin (VIII-2) (melting point=184° to 186° C., mass spectrum (M+)=430, yield=86.4%).

後処理

  1. customThe mixture was reacted
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was poured into ice water
  4. filtrationThe precipitated crystals were filtered out
  5. customrecrystallized from methanol

出典と根拠

ORDレコード
ord-3d0d762737d34c2080eeda70e521dbc7
出典データセット
uspto-grants-1998_03
特許番号
US05731293

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