Epichlorohydrin → HCID 46232584, Verbindung

HRID 83106Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 83106
[OH:1][C:2]1[CH:3]=[C:4]2[C:13](=[C:14]([OH:16])[CH:15]=1)[C:12](=[O:17])[C:11]1[C:6](=[CH:7][CH:8]=[C:9]3[CH:21]=[CH:20][CH:19]=[CH:18][C:10]3=1)[O:5]2.[CH2:22]([CH:24]1[O:26][CH2:25]1)Cl>CC(C)=O>[OH:16][C:14]1[CH:15]=[C:2]([O:1][CH2:22][CH:24]2[CH2:25][O:26]2)[CH:3]=[C:4]2[C:13]=1[C:12](=[O:17])[C:11]1[C:6](=[CH:7][CH:8]=[C:9]3[CH:21]=[CH:20][CH:19]=[CH:18][C:10]3=1)[O:5]2

Komponenten

4

Edukt 2

HCID 7835EpichlorohydrinHCID 157102119,11-dihydroxy-12H-benzo(a)xanthen-12-one

Produkt 1

HCID 46232584HCID 46232584, VerbindungAusbeute 40,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
57.5 °C

Versuchsvorschrift

The compound 9,11-dihydroxy-12H-benzo[a]xanthen-12-one (0.1 g, 0.18 mmol) synthesized in Step 1 of Examples 14 and 15, CS2CO3 (0.36 g, 0.54 mmol), and anhydrous acetone (20 mL) were charged to a dry round-bottom flask. Under stirring, epichlorohydrin (0.2 g, 1.08 mmol) was added thereto using a syringe. The reaction liquid was stirred with reflux at a temperature of 55 to 60° C. under a nitrogen atmosphere (48 h). Solid of the reaction mixture was filtered and removed. 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 a yellow solid compound 11-hydroxy-9-(oxiran-2-ylmethoxy)-12H-benzo[a]xanthen-12-one (24.3 mg, 20.3%) and a yellow solid compound 9,11-bis(oxiran-2-ylmethoxy)-12H-benzo[a]xanthen-12-one (32 mg, 22.1%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-824ab6a2e584437499717807550403a6
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846749B2

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