Epithiochlorohydrin → 11-hydroxy-9-(thiiran-2-ylmethoxy)-12H-benzo[a]xanthen-12-one

HRID 83105

Reaktionsgleichung

[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]1[S:24][CH:23]1[CH2:25]Cl>CC(C)=O>[OH:16][C:14]1[CH:15]=[C:2]([O:1][CH2:25][CH:23]2[CH2:22][S:24]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

Reaktionsbedingungen

Temperatur: 57.5 °C

Versuchsvorschrift

9,11-dihydroxy-12H-benzo[a]xanthen-12-one (0.1 g, 0.18 mmol) prepared in Step 1 of Examples 14 and 15, CS2CO3 (0.36 g, 0.54 mmol), and anhydrous acetone (13 mL) were charged to a dry round-bottom flask, and epithiochlorohydrin (0.2 g, 1.08 mmol) dissolved in anhydrous acetone (2 mL) was added thereto with stirring. The reaction mixture was stirred with reflux overnight at a temperature of 55 to 60° C. under a nitrogen atmosphere. Solid of the reaction mixture was filtered, removed and 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-(thiiran-2-ylmethoxy)-12H-benzo[a]xanthen-12-one (27.3 mg, 21.7%) and a yellow solid compound 9,11-bis(thiiran-2-ylmethoxy)-12H-benzo[a]xanthen-12-one (31.2 mg, 20.5%).

Aufarbeitung

additionwas added
stirringThe reaction mixture was stirred
filtrationSolid of the reaction mixture was filtered
customremoved
concentrationconcentrated under reduced pressure
customThe resulting residue was separated
custompurified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:3 (v/v))

Quellen und Nachweise

ORD-Eintrag: ord-ad24439d2b614dd9810ed68150b04d5c
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08846749B2

Verknüpfte Notizen

Wird geladen…