ethyl 2-(9H-xanthen-9-yl)-2-(3-methoxy-4-methoxycarbonylbenzoyl)acetate → methyl 4-[2-(9H-xanthen-9-yl)acetyl]-2-methoxybenzoate

HRID 442793

Reaktionsgleichung

Reaktionsgleichung von HRID 442793
[CH:1]1[C:14]2[CH:13]([CH:15]([C:21](=[O:34])[C:22]3[CH:27]=[CH:26][C:25]([C:28]([O:30][CH3:31])=[O:29])=[C:24]([O:32][CH3:33])[CH:23]=3)C(OCC)=O)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1>CS(C)=O.O>[CH:1]1[C:14]2[CH:13]([CH2:15][C:21]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([O:30][CH3:31])=[O:29])=[C:24]([O:32][CH3:33])[CH:23]=3)=[O:34])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 1

HCID 54564584ethyl 2-(9H-xanthen-9-yl)-2-(3-methoxy-4-methoxycarbonylbenzoyl)acetate

Produkt 1

HCID 70091447methyl 4-[2-(9H-xanthen-9-yl)acetyl]-2-methoxybenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a solution of ethyl 2-(9H-xanthen-9-yl)-2-(3-methoxy-4-methoxycarbonylbenzoyl)acetate (7.0 g, 14.6 mmol) in dimethylsulphoxide (40 ml) was added water (0.53 ml, 29.3 mmol). The solution was stirred under an atmosphere of nitrogen at reflux for 1.5 h before cooling and diluting with water. The mixture was extracted with dichloromethane (3×) and the combined extracts washed with water (5×) and a saturated solution of sodium chloride. The organic phase was dried over magnesium sulphate, filtered and evaporated to a yellow oil. Purification on flash silica eluting with dichloromethane-hexane (3:2 then 4:1) gave a solid which was crystallised from methanol to give methyl 4-[2-(9H-xanthen-9-yl)acetyl]-2-methoxybenzoate as a yellow solid.

Aufarbeitung

  1. temperatureat reflux for 1.5 h
  2. temperaturebefore cooling
  3. extractionThe mixture was extracted with dichloromethane (3×)
  4. washthe combined extracts washed with water (5×)
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated to a yellow oil
  8. customPurification on flash silica eluting with dichloromethane-hexane (3:2
  9. custom4:1) gave a solid which
  10. customwas crystallised from methanol

Quellen und Nachweise

ORD-Eintrag
ord-afd566b718b54e6c8494e5def3429f1d
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05891899

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