Dimethyl Sulfate → Ethyl 3-iodo-2,4-dimethoxy-6-methylbenzoate

HRID 2177847Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2177847
O[C:2]1[C:12]([I:13])=[C:11]([OH:14])[CH:10]=[C:9]([CH3:15])[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].COS([O:21][CH3:22])(=O)=O.[C:23](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[I:13][C:12]1[C:2]([O:21][CH3:22])=[C:3]([C:9]([CH3:15])=[CH:10][C:11]=1[O:14][CH3:23])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Komponenten

5

Edukt 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 10519838Ethyl 2,4-dihydroxy-3-iodo-6-methylbenzoate2×

Produkt 1

HCID 10915077Ethyl 3-iodo-2,4-dimethoxy-6-methylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of ethyl 2,4-dihydroxy-3-iodo-6-methylbenzoate (Intermediate 204, 0.144 g), dimethylsulphate (0.085 ml) and potassium carbonate (0.185 g) in acetone (10 ml) was heated at reflux for 2.5 hours. After cooling, the mixture was filtered and the filtrate was evaporated to dryness. The residue was partitioned between DCM and water and the organic layer was filtered through a phase separator. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-20% to give ethyl 3-iodo-2,4-dimethoxy-6-methylbenzoate (0.158 g).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 hours
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered
  5. customthe filtrate was evaporated to dryness
  6. customThe residue was partitioned between DCM and water
  7. filtrationthe organic layer was filtered through a phase separator
  8. customThe filtrate was evaporated to dryness
  9. customthe residue was purified by chromatography on silica
  10. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-20%

Quellen und Nachweise

ORD-Eintrag
ord-f6743098a12149aeab07f5b8dc351dcb
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067905B2

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