Allyl bromide → HCID 11002836, 화합물

HRID 1459060노트

반응식

HRID 1459060 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 11002836HCID 11002836, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-27c9e34144a5435fa66d69f412d4736b
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05852213

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