Allyl bromide → HCID 11002836, compound

HRID 1459060Notes

Reaction equation

HRID 1459060 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 11002836HCID 11002836, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-27c9e34144a5435fa66d69f412d4736b
Source dataset
uspto-grants-1998_12
Patent number
US05852213

Reaction notes

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