Triethylamine → 4-Phenyl-1-(3-phenylazetidin-1-yl)butan-1-one

HRID 1404458Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1404458
[C:1]1([CH:7]2[CH2:10][NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]1([CH2:17][CH2:18][CH2:19][C:20](Cl)=[O:21])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl>[C:11]1([CH2:17][CH2:18][CH2:19][C:20]([N:9]2[CH2:10][CH:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:8]2)=[O:21])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 117898654-Phenylbutanoyl ChlorideHCID 289015863-Phenylazetidine

Produkt 1

HCID 672889534-Phenyl-1-(3-phenylazetidin-1-yl)butan-1-oneAusbeute 83,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 3-phenylazetidine (266 mg, 2 mmol) in dry dichloromethane (6 mL) is cooled in an ice bath, and 4-phenylbutyryl chloride (456.6 mg, 2.5 mmol, 1.25 eq) and triethylamine (417 μL, 3 mmol, 1.5 eq) are added. After stirring for 6 hours at room temperature the reaction mixture is diluted with dichloromethane (10 mL). The organic solution is subsequently washed with 1 M KHSO4, 5% NaHCO3 and brine. After drying over Na2SO4, dichloromethane is removed in vacuo and the crude material is purified by flash chromatography (silicagel, ethyl acetate/toluene 1:5). The fractions containing 4-phenyl-1-(3-phenylazetidin-1-yl)butan-1-one are collected and the solvent is removed in vacuo to give 467 mg of colorless oil.

Aufarbeitung

  1. washThe organic solution is subsequently washed with 1 M KHSO4, 5% NaHCO3 and brine
  2. dry with materialAfter drying over Na2SO4, dichloromethane
  3. customis removed in vacuo
  4. customthe crude material is purified by flash chromatography (silicagel, ethyl acetate/toluene 1:5)
  5. additionThe fractions containing 4-phenyl-1-(3-phenylazetidin-1-yl)butan-1-one
  6. customare collected
  7. customthe solvent is removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d194c57b812e4eb3ab00ba75dd9f5b33
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912329B2

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