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N,N-Dimethylcyclopropanecarboxamide → Cyclopropyl[4-[1-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)-1-methylethyl]phenyl]methanone

HRID 446047
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 446047
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:17])([CH3:16])[C:9]2[O:10][CH2:11][C:12]([CH3:15])([CH3:14])[N:13]=2)=[CH:4][CH:3]=1.C([Li])CCC.CN(C)[C:25]([CH:27]1[CH2:29][CH2:28]1)=[O:26]>C1COCC1>[CH:27]1([C:25](=[O:26])[C:2]2[CH:7]=[CH:6][C:5]([C:8]([CH3:17])([CH3:16])[C:9]3[O:10][CH2:11][C:12]([CH3:15])([CH3:14])[N:13]=3)=[CH:4][CH:3]=2)[CH2:29][CH2:28]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 140273N,N-DimethylcyclopropanecarboxamideHCID 155123902-[2-(4-Bromophenyl)propan-2-yl]-4,4-dimethyl-4,5-dihydro-1,3-oxazoleHCID 178418339Butyllithium

Produkt 1

HCID 24720860Cyclopropyl[4-[1-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)-1-methylethyl]phenyl]methanoneAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A solution of 4-bromo-α,α-dimethyl-α-(4,4-dimethyloxazolin-2-yl)toluene, prepared according to Example 2, (10.0 g. 0.0338 mole) in 400 mL THF was cooled to −78° C., n-butyllithium (16 mL, 0.042 mole) was added via syringe, and the mixture was stirred at −78° C. for 30 minutes. While keeping the temperature below −75° C., N,N-dimethyl cyclopropylcarboxylic acid amide (11.5 g, 0.102 mole) in 30 mL THF was added dropwise, and the mixture was stirred at −78° C. for 30 minutes. The mixture was allowed to warm to −15° C., and was quenched with water. The product was extracted with methylene chloride, washed with saturated NaCl solution, dried over Na2SO4, and concentrated. The residue was cooled to 0° C., treated with minimal acetonitrile, and filtered, to afford 6.95 g of 4-(cyclopropyl-oxo-methyl)-α,α-dimethyl-α-(4,4-dimethyloxazolin-2-yl)toluene as a white solid (72%).

Aufarbeitung

  1. additionwas added dropwise
  2. stirringthe mixture was stirred at −78° C. for 30 minutes
  3. temperatureto warm to −15° C.
  4. customwas quenched with water
  5. extractionThe product was extracted with methylene chloride
  6. washwashed with saturated NaCl solution
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. temperatureThe residue was cooled to 0° C.
  10. additiontreated with minimal acetonitrile
  11. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-777c80c668ed4281abd7e165b30cedb2
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08476445B2

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