Epichlorohydrin → 1-hydroxy-3-(oxiran-2-ylmethoxy)-9H-xanthen-9-one

HRID 83093

反応式

HRID 83093 の反応式
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:7][C:6]=2[CH:5]=[C:4]([OH:17])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:24]([CH:26]1[O:28][CH2:27]1)Cl>CC(C)=O>[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:7][C:6]=2[CH:5]=[C:4]([O:17][CH2:24][CH:26]2[CH2:27][O:28]2)[CH:3]=1

参加物

5

反応物 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 54881931,3-Dihydroxy-xanthone

生成物 1

HCID 105171431-hydroxy-3-(oxiran-2-ylmethoxy)-9H-xanthen-9-one収率 22.4%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
57.5 °C

実験手順

1,3-dihydroxy-9H-xanthen-9-one (1 g, 4.39 mmol) prepared in Step 1 of Example 2 and K2CO3 (1.52 g, 10.98 mmol) were added to a dry round-bottom flask, and anhydrous acetone (25 ml) was added thereto. Epichlorohydrin (1.73 mL, 21.95 mmol) was added dropwise to the reaction mixture, and the reaction liquid was stirred under reflux at a temperature of 55 to 60° C. for 6 hours. After the reaction was completed, the solvent was removed under reduced pressure. The resulting residue was separated and purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:1 (v/v)) to give the title compound (0.28 g, 22%) as a light brown solid.

後処理

  1. customthe reaction liquid
  2. customthe solvent was removed under reduced pressure
  3. customThe resulting residue was separated
  4. custompurified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:1 (v/v))

出典と根拠

ORDレコード
ord-07e7999c8d4f4167b703d2f440767984
出典データセット
uspto-grants-2014_09
特許番号
US08846749B2

関連ノート

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