2-Tert-Butylphenol → 1-Benzhydryl-3-(2-tert-butylphenoxy)azetidine

HRID 2041958

Reaktionsgleichung

Reaktionsgleichung von HRID 2041958
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH2:11][CH:10](CS([O-])(=O)=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:23]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[OH:33])([CH3:26])([CH3:25])[CH3:24].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH:7]([N:8]1[CH2:11][CH:10]([O:33][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[C:23]([CH3:26])([CH3:24])[CH3:25])[CH2:9]1)([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

7

Edukt 3

HCID 69232-Tert-ButylphenolHCID 14798Sodium HydroxideHCID 71431707(1-Benzhydrylazetidin-3-yl)methanesulfonate

Produkt 1

HCID 595771511-Benzhydryl-3-(2-tert-butylphenoxy)azetidineAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A stirred solution of 1-(diphenylmethyl)-3-azetidinylmethane sulfonate (12.68 g, 39.9 mmol), 2-tert-butylphenol (6.0 g, 39.9 mmol), tetrabutylammonium bromide (1.29 g, 3.99 g) and sodium hydroxide (15.0 mL of 8.0 M solution in water, 120 mmol) in toluene (40 mL) was heated at 100° C. for 5 h. Then, the reaction mixture was cooled to room temperature, diluted with ethyl acetate and separated. The organic layer was washed with water, saturated sodium chloride, dried (Na2SO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, 100:0 to 98:2 heptane/ethyl acetate) provided impure 1-benzhydryl-3-(2-tert-butylphenoxy)azetidine (9.10 g, 66%) as a yellow oil, which was used without further purification or characterization.

Aufarbeitung

  1. customseparated
  2. washThe organic layer was washed with water, saturated sodium chloride
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash column chromatography (silica gel, 100:0 to 98:2 heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-f0c2bbc265c3435f9635c8661fef487f
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586571B2

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