Diethyl Ether → 2-(3-Chloro-2-methylsulphenylphenyl)-4,4-dimethyloxazoline

HRID 266537Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 266537
C([Li])CCC.[Cl:6][C:7]1[CH:8]=[C:9]([C:13]2[O:14][CH2:15][C:16]([CH3:19])([CH3:18])[N:17]=2)[CH:10]=[CH:11][CH:12]=1.[CH3:20][S:21]SC.CCOCC>C1COCC1>[Cl:6][C:7]1[C:8]([S:21][CH3:20])=[C:9]([C:13]2[O:14][CH2:15][C:16]([CH3:19])([CH3:18])[N:17]=2)[CH:10]=[CH:11][CH:12]=1

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 12232Dimethyl DisulfideHCID 10798476Oxazole, 2-(3-chlorophenyl)-4,5-dihydro-4,4-dimethyl-HCID 178418339Butyllithium

Produkt 1

HCID 544052592-(3-Chloro-2-methylsulphenylphenyl)-4,4-dimethyloxazolineAusbeute 96,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-65 °C

Versuchsvorschrift

n-Butyllithium (2.5M in hexane, 4.2 ml) was added to a solution of 2-(3-chlorophenyl)-4,4-dimethyloxazoline (2 g) in THF while maintaining the temperature below -45° C. The mixture was stirred at -65° C. for 3 hours. Dimethyl disulphide (1.0 g) was added and the mixture was stirred at -65° C. for 2.5 hours and allowed to warm to room temperature. Ether was added and the mixture was washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give 2-(3-chloro-2-methylsulphenylphenyl)-4,4-dimethyloxazoline (2.35 g) as a yellow oil NMR (CDCl3) 2.0(s,6H) 3.0(s,3H) 4.65(s,2H) 7.5-8.1(m,3H).

Aufarbeitung

  1. temperaturewhile maintaining the temperature below -45° C
  2. stirringthe mixture was stirred at -65° C. for 2.5 hours
  3. temperatureto warm to room temperature
  4. washthe mixture was washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-8153ad61b19f4ffc9968adb0773c4d5e
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05650533

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