Allyl bromide → HCID 11002836, Verbindung

HRID 1459060Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1459060
[O:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].C([N-]C(C)C)(C)C.[Li+].[CH2:15](Br)[CH:16]=[CH2:17].[CH3:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].[CH2:26]1[CH2:30][O:29][CH2:28][CH2:27]1.[CH:31]1[CH:36]=[CH:35]C=[CH:33][CH:32]=1>C1COCC1>[CH2:19]([C@H:4]1[CH2:5][O:1][C:2](=[O:6])[N:3]1[C:28](=[O:29])[C@H:27]([CH2:26][CH2:30][CH2:33][CH2:32][CH2:31][CH2:36][CH3:35])[CH2:15][CH:16]=[CH2:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

6

Edukt 4

HCID 7841Allyl bromideHCID 739492-OxazolidinoneHCID 2724682Lithium diisopropylamideHCID 86600160Heptane tetrahydrofuran benzene

Produkt 1

HCID 11002836HCID 11002836, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 5.50 g (0.017 mol) of the oxazolidinone in 40 mL of THF, cooled to -78 ° C., was added 17.3 mL (0.035 mol) of a 2.0M solution of lithium diisopropylamide in heptane/THF/benzene. The resulting mixture was stirred at -78° C. for 1 h and then neat allyl bromide (7.5 mL, 0.087 mol) was added to the reaction mixture. The reaction was allowed to warm to 0 degrees (ice bath) and stirred for an additional 3 h and then quenched with 5% HCl solution. The resulting mixture was extracted with ether and the combined organic layers were washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:10) to provide 5.0 g (81%) of the desired allylated product as a colorless oil. Electrospray Mass Spec: 358.2 (M+H)+.

Aufarbeitung

  1. temperatureto warm to 0 degrees (ice bath)
  2. stirringstirred for an additional 3 h
  3. customquenched with 5% HCl solution
  4. extractionThe resulting mixture was extracted with ether
  5. washthe combined organic layers were washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:10)
  10. customto provide 5.0 g (81%) of the

Quellen und Nachweise

ORD-Eintrag
ord-27c9e34144a5435fa66d69f412d4736b
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05852213

Notizen zur Reaktion

Wird geladen…