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Epichlorohydrin → 1-hydroxy-5-methoxy-3-(oxiran-2-ylmethoxy)-9H-xanthen-9-one

HRID 83090
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HRID 83090 반응식
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([O:17][CH3:18])[CH:10]=[CH:11][CH:12]=3)[O:7][C:6]=2[CH:5]=[C:4]([OH:19])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:26]([CH:28]1[O:30][CH2:29]1)Cl>CC(C)=O>[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([O:17][CH3:18])[CH:10]=[CH:11][CH:12]=3)[O:7][C:6]=2[CH:5]=[C:4]([O:19][CH2:26][CH:28]2[CH2:29][O:30]2)[CH:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 120264891,3-dihydroxy-5-methoxy-9H-xanthen-9-one

생성물 1

HCID 444324121-hydroxy-5-methoxy-3-(oxiran-2-ylmethoxy)-9H-xanthen-9-one수율 32.1%

시약·촉매·용매 1

HCID 180Acetone용매

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온도
57.5 °C

실험 절차

A mixture of 1,3-dihydroxy-5-methoxy-9H-xanthen-9-one (1.13 g, 4.39 mmol) prepared in Step 1 of Example 1 and K2CO3 (1.52 g, 10.98 mmol) in anhydrous acetone (25 mL) was charged to a dry round-bottom flask, and epichlorohydrin (1.73 mL, 21.95 mmol) was added thereto, followed by stirring under reflux at a temperature of 55 to 60° C. for 6 hours. Solid of the reaction mixture was filtered, and 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 (443.2 mg, 32%) as a light yellow solid.

후처리

  1. additionwas charged to a dry round-bottom flask
  2. filtrationSolid of the reaction mixture was filtered
  3. customthe solvent was removed under reduced pressure
  4. customThe resulting residue was separated
  5. custompurified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:1 (v/v))

출처 및 근거

ORD 기록
ord-d4ca5081a38d40908201b58b26d90f95
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08846749B2

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