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

HRID 83093

반응식

HRID 83093 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
57.5 °C

실험 절차

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.

후처리

  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))

출처 및 근거

ORD 기록
ord-07e7999c8d4f4167b703d2f440767984
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846749B2

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