Citric Acid → HCID 21967943、化合物

HRID 1003936ノート

反応式

HRID 1003936 の反応式
[O:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][C:12]([C:14]3[C:19]([O:20][CH2:21][CH:22]=[CH2:23])=[CH:18][C:17]([CH3:24])=[CH:16][C:15]=3[O:25][C@@H:26]3[O:34][C@H:33]([CH2:35][OH:36])[C@@H:31]([OH:32])[C@H:29]([OH:30])[C@H:27]3[OH:28])=[O:13])[CH:8]=[CH:9][C:2]1=2.C(=O)=O.CC(C)=O.Cl[C:45]([O:47][CH3:48])=[O:46].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>N1C(C)=CC(C)=CC=1C.ClCCl>[O:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][C:12]([C:14]3[C:19]([O:20][CH2:21][CH:22]=[CH2:23])=[CH:18][C:17]([CH3:24])=[CH:16][C:15]=3[O:25][C@@H:26]3[O:34][C@H:33]([CH2:35][O:36][C:45]([O:47][CH3:48])=[O:46])[C@@H:31]([OH:32])[C@H:29]([OH:30])[C@H:27]3[OH:28])=[O:13])[CH:8]=[CH:9][C:2]1=2

参加物

7

反応物 4

HCID 311Citric AcidHCID 6586Methyl chloroformateHCID 10601391HCID 10601391、化合物HCID 18522661Acetone cardice

生成物 1

HCID 21967943HCID 21967943、化合物収率 87.2%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 79532,4,6-Trimethylpyridine溶媒

実験手順

3-(5-Benzo[b]furanyl)-2'-(β-D-glucopyranosyloxy)-6'-allyloxy-4'-methylpropiophenone (500 mg) is dissolved in 2,4,6-collidine (5 ml), and the mixture is cooled to 40° C. with dry ice-acetone, and thereto is added dropwise a solution of methyl chloroformate (114 mg) in dichloromethane (0.5 ml) with stirring. The mixture is stirred at 40° C. for one hour, and stirred at room temperature for 1.5 hour. The reaction mixture is poured into cold 10% aqueous citric acid solution, and the mixture is extracted with ethyl acetate. The organic layer is washed with water, dried, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (solvent; chloroform/methanol) to give 3-(5-benzo[b]furanyl)-2'-(6-O-methoxycarbonyl-β-D-glucopyranosyloxy)-6'-allyloxy-4'-methylpropiophenone (487 mg).

後処理

  1. stirringThe mixture is stirred at 40° C. for one hour
  2. stirringstirred at room temperature for 1.5 hour
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe organic layer is washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue is purified by silica gel column chromatography (solvent; chloroform/methanol)

出典と根拠

ORDレコード
ord-2e55ee8970be49a6a8b07a7ae20e825a
出典データセット
uspto-grants-2000_04
特許番号
US06048842

反応ノート

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