Benzoyl chloride → (3-(2-Tert-butylphenoxy)azetidin-1-yl)(phenyl)methanone

HRID 2041975

Reaktionsgleichung

Reaktionsgleichung von HRID 2041975
[C:1]([C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[O:7][CH:8]1[CH2:11][NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1.C(OCC)(=O)C>[C:1]([C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[O:7][CH:8]1[CH2:9][N:10]([C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:30])[CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 534095303-(2-Tert-butylphenoxy)azetidine

Produkt 1

HCID 59577245(3-(2-Tert-butylphenoxy)azetidin-1-yl)(phenyl)methanoneAusbeute 46,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-(2-tert-butylphenoxy)azetidine (0.30 g, 1.46 mmol) and triethylamine (0.16 g, 1.61 mmol) in THF (10.0 mL) was added benzoyl chloride (0.23 g, 1.61 mmol). After stirring for 16 h at room temperature, the reaction mixture was diluted with ethyl acetate, washed with water, saturated sodium chloride, dried (Na2SO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography (silica gel; 85:15 to 50:50 heptane/ethyl acetate) provided (3-(2-tert-butylphenoxy)azetidin-1-yl)(phenyl)methanone (0.21 g, 46%) as a yellow solid.

Aufarbeitung

  1. washwashed with water, saturated sodium chloride
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash column chromatography (silica gel; 85:15 to 50:50 heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-f917dc7185294bf3bf6efc6124a64456
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586571B2

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