Methyl iodide → 1-(4-Bromo-3-methoxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl) ethanone

HRID 2180592Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2180592
[Br:1][C:2]1[C:11]2[C:10]([CH3:13])([CH3:12])[CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([C:14](=[O:16])[CH3:15])[C:3]=1[OH:17].[C:18](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O.O>[Br:1][C:2]1[C:11]2[C:10]([CH3:12])([CH3:13])[CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([C:14](=[O:16])[CH3:15])[C:3]=1[O:17][CH3:18]

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 224908841-(4-Bromo-3-hydroxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone

Produkt 1

HCID 224910531-(4-Bromo-3-methoxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl) ethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 1-(4-bromo-3-hydroxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone (Compound A-91, 11.8 g, 39.7 mmol), potassium carbonate (14.4 g, 119.1 mmol) in acetone (350 mL) was added methyl iodide (19.8 mL, 317.6 mmol). After heating to reflux for 16 h, the mixture was cooled to room temperature, diluted with water and extracted with diethyl ether. The combined ethereal layers were washed with water, brine, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a yellow oil. The material was used in the next step without further purification.

Aufarbeitung

  1. temperatureAfter heating
  2. temperatureto reflux for 16 h
  3. extractionextracted with diethyl ether
  4. washThe combined ethereal layers were washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f741ea382cf947f3b25a9aeb7ec0ae8a
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06887896B1

Notizen zur Reaktion

Wird geladen…