Allyl bromide → HCID 11002836、化合物

HRID 1955425ノート

反応式

HRID 1955425 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 11002836HCID 11002836、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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 alkylated product as a colorless oil. Electrospray Mass Spec: 358.2 (M+H)+.

後処理

  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

出典と根拠

ORDレコード
ord-c9de873b1f9b407bafac88e0395432a7
出典データセット
uspto-grants-2000_09
特許番号
US06124502

反応ノート

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