Epichlorohydrin → 1,3-bis(oxiran-2-ylmethoxy)-12H-benzo[b]xanthen-12-one

HRID 83110

반응식

HRID 83110 반응식
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[CH:12]=[C:11]4[CH:17]=[CH:18][CH:19]=[CH:20][C:10]4=[CH:9][C:8]=3[O:7][C:6]=2[CH:5]=[C:4]([OH:21])[CH:3]=1.[CH2:22]([CH:24]1[O:26][CH2:25]1)Cl>CC(C)=O>[O:26]1[CH2:25][CH:24]1[CH2:22][O:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[CH:12]=[C:11]4[CH:17]=[CH:18][CH:19]=[CH:20][C:10]4=[CH:9][C:8]=3[O:7][C:6]=2[CH:5]=[C:4]([O:21][CH2:22][CH:24]2[CH2:25][O:26]2)[CH:3]=1

참가 물질

4

반응물 2

HCID 7835EpichlorohydrinHCID 107077051,3-dihydroxy-12H-benzo(b)xanthen-12-one

생성물 1

HCID 462326481,3-bis(oxiran-2-ylmethoxy)-12H-benzo[b]xanthen-12-one수율 21.8%

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
57.5 °C

실험 절차

1,3-dihydroxy-12H-benzo[b]xanthen-12-one (0.15 g, 0.54 mmol) synthesized in Step 1 of Example 18, CS2CO3 (0.53 g, 1.62 mmol), and anhydrous acetone (30 mL) were charged to a dry round-bottom flask, and epichlorohydrin (0.25 g, 2.7 mmol) was added thereto with stirring using a syringe. The reaction mixture was stirred with reflux under a nitrogen atmosphere (55 to 60° C., overnight). Solid of the reaction mixture was filtered and removed, and the filtrate was concentrated under reduced pressure. The resulting residue was separated and purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:3 (v/v)) to give the title compound (15.3 mg, 21.8%) as a yellow solid.

후처리

  1. stirringThe reaction mixture was stirred
  2. filtrationSolid of the reaction mixture was filtered
  3. customremoved
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was separated
  6. custompurified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:3 (v/v))

출처 및 근거

ORD 기록
ord-1d03c9ea32d24eaebcef6e626a5f8f1c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846749B2

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