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Hexane → (S)-4-benzyl-3-butyryloxazolidin-2-one

HRID 1634528
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1634528
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.CCCCCC.[C:25](Cl)(=[O:29])[CH2:26][CH2:27][CH3:28].[Cl-].[NH4+]>O1CCCC1>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:25](=[O:29])[CH2:26][CH2:27][CH3:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 8058HexaneHCID 8855Butyryl chlorideHCID 25517Ammonium ChlorideHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 178418339Butyllithium

Produkt 1

HCID 11010277(S)-4-benzyl-3-butyryloxazolidin-2-oneAusbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

(S)-4-benzyl-2-oxazolidinone (2.26 g, 15.0 mmol) and 30 ml of dehydrated tetrahydrofuran were mixed, which was cooled to −78° C. under an atmosphere of argon. Under stirring, 1.6 mol/l solution of n-butyl lithium in hexane (10.3 ml, 16.5 mmol) was added dropwise for over 10 minutes and the mixture was stirred for 30 minutes as it was. Next, butyryl chloride (1.56 ml, 15.0 mmol) dissolved into 30 ml of dehydrated tetrahydrofuran was added dropwise for over 10 minutes and the mixture was stirred for 30 minutes, followed by stirring for 3 hours at room temperature. Saturated aqueous solution of ammonium chloride was added to the reaction mixture and concentrated. Water was added to the residue, which was extracted with ethyl acetate. The extract was washed with water and with brine, then dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=1:1 v/v) to obtain 3.64 g (98%) of the title compound as a colorless oil.

Aufarbeitung

  1. stirringthe mixture was stirred for 30 minutes as it
  2. additionwas added dropwise for over 10 minutes
  3. stirringthe mixture was stirred for 30 minutes
  4. stirringby stirring for 3 hours at room temperature
  5. concentrationconcentrated
  6. additionWater was added to the residue, which
  7. extractionwas extracted with ethyl acetate
  8. washThe extract was washed with water and with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated
  11. customThe residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=1:1 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-46352f7e80e94cb4959dfe34e5aec7e8
Quelldatensatz
uspto-grants-2003_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06506797B1

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