tert-BUTYL CHLORIDE → 2-Tert-butyl-4-phenyl-cyclohexanone

HRID 12059

Reaktionsgleichung

Reaktionsgleichung von HRID 12059
C[Si](C)(C)[O:3][C:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6][CH:5]=1.[C:18](Cl)([CH3:21])([CH3:20])[CH3:19]>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[C:18]([CH:5]1[CH2:6][CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:9][C:4]1=[O:3])([CH3:21])([CH3:20])[CH3:19]

Komponenten

5

Edukt 2

HCID 10486tert-BUTYL CHLORIDEHCID 110860724-Phenyl-1-trimethylsilyloxy-1-cyclohexene

Produkt 1

HCID 686807642-Tert-butyl-4-phenyl-cyclohexanoneAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
-45 °C

Versuchsvorschrift

Trimethyl-(4-phenyl-cyclohex-1-enyloxy)-silane (7.27 mmol) and tert-butyl chloride (7.85 mmol) are introduced first in dichloromethane under nitrogen and cooled to −45° C. A solution, also cooled to −45° C., of titanium tetrachloride (7.63 mmol) in dichloromethane (3.6 ml) is added, and stirring is continued for 3 hours at this temperature. The reaction mixture is diluted with dichloromethane and washed with ice water. The organic phase is dried over sodium sulphate and the solvent is removed in a vacuum. Column chromatography (ethyl acetate/heptane 1:4) of the residue produces the title compound (250 mg) in a yield of 15% (Angew Chem Int Ed Engl 1978, 17, 1, 48-49). 1H NMR (ppm, CDCl3): 7.35 (5H); 3.15 (1H); 2.55 (1H); 2.4 (3H); 2.25 (1H); 2 (1H); 1.8 (1H); 1.05 (9H).

Aufarbeitung

  1. additionis added
  2. washwashed with ice water
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. customthe solvent is removed in a vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1b1a75c210864a4abfc772d05a463448
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727979B2

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