Hexane → HCID 21187685, Verbindung

HRID 1383775Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1383775
[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:13]([CH:14]3[CH2:16][CH2:15]3)[O:12][C:11](=[O:17])[NH:10]2)[CH:5]=[CH:6][C:7]=1[F:8].C([Li])CCC.CCCCCC.[CH:29]1[C:34]([N+:35]([O-:37])=[O:36])=[CH:33][CH:32]=[C:31]([Cl-]C([O-])=O)[CH:30]=1.[C:42](=O)([OH:44])[O-:43].[Na+]>C1COCC1>[N+:35]([C:34]1[CH:29]=[CH:30][C:31]([O:44][C:42]([N:10]2[CH:9]([C:4]3[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=3)[CH:13]([CH:14]3[CH2:15][CH2:16]3)[O:12][C:11]2=[O:17])=[O:43])=[CH:32][CH:33]=1)([O-:37])=[O:36]

Komponenten

6

Edukt 4

HCID 8058HexaneHCID 516892Sodium BicarbonateHCID 22993473HCID 22993473, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 21187685HCID 21187685, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 4-(3,4-difluorophenyl)-5-cyclopropyl-oxazolidin-2-one (2 g, 8.3 mmol) in 100 mL THF was added a solution of n-butyllithium in hexane (9.1 mmol) dropwise via a syringe under an argon atmosphere at −78° C. The resulting yellow solution was stirred at −78° C. for 10 min. To this solution was then added dropwise via syringe 4-nitrophenylchloroformate (1.03 g, 5.1 mmol) in 20 mL of THF. The reaction was stirred at −78° for 10 min. The reaction mixture was poured into saturated sodium bicarbonate and extracted with ethyl acetate (2×200 mL). The organic extracts were washed with brine, and the organic layer was dried over Na2SO4. The solvent was removed after filtration, and the residue was purified by column chromatography on silica gel 30% ethyl acetate hexane. The material was rechromatographed on silica gel eluting with 2% acetone/methylene chloride ti) give 1.2 g the product as a thick syrup which solidified upon standing.

Aufarbeitung

  1. stirringThe reaction was stirred at −78° for 10 min
  2. extractionextracted with ethyl acetate (2×200 mL)
  3. washThe organic extracts were washed with brine
  4. dry with materialthe organic layer was dried over Na2SO4
  5. customThe solvent was removed
  6. filtrationafter filtration
  7. customthe residue was purified by column chromatography on silica gel 30% ethyl acetate hexane
  8. customThe material was rechromatographed on silica gel eluting with 2% acetone/methylene chloride ti)

Quellen und Nachweise

ORD-Eintrag
ord-6f9e6bb1a63f43e0846c9ccd65a85520
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06255315B1

Notizen zur Reaktion

Wird geladen…