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

HRID 1597766

反応式

HRID 1597766 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 [VIII] (1.0 g), benzyl chloride (1.0 g), potassium carbonate (0.7 g), a catalytic amount of 18-crown-6-ether and potassium iodide, and dimethylformamide (40 ml) were added to an eggplant-shaped flask (100 ml). The mixture was stirred at 60° C. for 8 hours to cause a reaction. 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-glucosyloxycoumarin (VII-1) (melting point=184° to 186° C, mass spectrum (M+)=430, yield =86.4%).

後処理

  1. customa reaction
  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-98904fd5cb18417d95f30b25c2f04850
出典データセット
uspto-grants-1998_04
特許番号
US05736522

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