p-METHYLACETOPHENONE → alpha-Cyclopropyl-alpha,4-dimethylbenzenemethanol

HRID 561461

Reaktionsgleichung

Reaktionsgleichung von HRID 561461
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][CH:8]=1>C1COCC1.C(OCC)C>[CH:1]1([C:13]([C:10]2[CH:11]=[CH:12][C:7]([CH3:6])=[CH:8][CH:9]=2)([OH:15])[CH3:14])[CH2:3][CH2:2]1

Komponenten

5

Edukt 2

HCID 8500p-METHYLACETOPHENONEHCID 178418630HCID 178418630, Verbindung2×

Produkt 1

HCID 98258alpha-Cyclopropyl-alpha,4-dimethylbenzenemethanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

27 ml (26.8 mmol) of 1N cyclopropylmagnesium bromide solution in THF were added to 3.00 g (22.4 mmol) of 1-(4-methylphenyl)ethanone in 60 ml of diethyl ether at RT, and the mixture was stirred at RT overnight. Then a further 11 ml (11.2 mmol) of 1N cyclopropylmagnesium bromide solution in THF were added, and the mixture was stirred at RT overnight. The reaction mixture was added to ice-water, the phases were separated, the aqueous phase was extracted with dichloromethane, and the combined organic phases were dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate gradient with addition of 0.1% triethylamine) to result in 491 mg (13% of theory) of the title compound.

Aufarbeitung

  1. stirringthe mixture was stirred at RT overnight
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted with dichloromethane
  4. dry with materialthe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate gradient with addition of 0.1% triethylamine)

Quellen und Nachweise

ORD-Eintrag
ord-c1709cb70138446aa871527e8b3fb398
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063234B2

Verknüpfte Notizen

Wird geladen…