Sodium Chloride → (S)-3-Hept-6-enoyl-4-isopropyl-oxazolidin-2-one

HRID 1638186Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1638186
[CH:1]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[NH:5]1)([CH3:3])[CH3:2].[Li]CCCC.[C:15](Cl)(=[O:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21].[Na+].[Cl-]>C1COCC1.CCCCCC>[C:15]([N:5]1[C@@H:4]([CH:1]([CH3:3])[CH3:2])[CH2:8][O:7][C:6]1=[O:9])(=[O:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21]

Komponenten

7

Edukt 4

HCID 5234Sodium ChlorideHCID 7157133(4S)-4-(propan-2-yl)-1,3-oxazolidin-2-oneHCID 108556156-Heptenoyl chlorideHCID 178418339Butyllithium

Produkt 1

HCID 11053746(S)-3-Hept-6-enoyl-4-isopropyl-oxazolidin-2-oneAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

A solution of 2.08 g (16.10 mmol, 1 equivalent) of (4S)-4-isopropyl-oxazolidin-2-one in 15 ml of THF is cooled to -78° C. and mixed drop by drop with 11.6 ml (18.52 mmol, 1.15 equivalents) of a 1.6 M solution of n-BuLi solution in hexane. Then, a solution of 2.95 g (20.13 mmol, 1.25 equivalents) of hept-6-enoyl chloride in 10 ml of THF is added at -78° C. It is allowed to heat to room temperature, and the reaction solution is poured onto saturated NaCl solution. The aqueous phase is extracted with ether, the combined organic phases are dried on MgSO4, and the solvent is distilled off in a rotary evaporator. The residue is purified by column chromatography with PE:DE=3:1. 3.55 g (14.82 mmol, 92%) of oxazolidinone 21 is obtained as a colorless oil.

Aufarbeitung

  1. extractionThe aqueous phase is extracted with ether
  2. customthe combined organic phases are dried on MgSO4
  3. distillationthe solvent is distilled off in a rotary evaporator
  4. customThe residue is purified by column chromatography with PE

Quellen und Nachweise

ORD-Eintrag
ord-7f2505819c1b4c848d276efcf12096f4
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06043372

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