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Phenethyl bromide → HCID 9909367, 화합물

HRID 1636893
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HRID 1636893 반응식
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:14](=[O:22])[CH:15]([F:21])[CH:16]([F:20])[C:17]([OH:19])=[O:18].C([N-]C(C)C)(C)C.[Li+].[CH2:31](Br)[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>O1CCCC1>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:14](=[O:22])[CH:15]([F:21])[C:16]([F:20])([CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:17]([OH:19])=[O:18]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 7666Phenethyl bromideHCID 2724682Lithium diisopropylamideHCID 9796476HCID 9796476, 화합물

생성물 1

HCID 9909367HCID 9909367, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

To a solution of 4-dibenzofuran-2-yl-2,3-difluoro-4-oxo-butyric acid (1 equivalent, Example 6) in tetrahydrofuran cooled to -78° C. is added dropwise a solution of lithium diisopropylamide (2 equivalents). After stirring at -78° C. for 30 minutes, a solution of phenethyl bromide (1 equivalent) in tetrahydrofuran is added. The cooling bath is removed, and the reaction mixture gradually warms to room temperature and is stirred overnight. To this solution is added aqueous HCl (1 M) and ethyl acetate. The layers are separated, and the organic portion is washed with brine, dried (MgSO4), and concentrated in vacuo. The title compound is obtained by separation from the reaction by-product using silica gel chromatography (elution with chloroform/methanol).

후처리

  1. customThe cooling bath is removed
  2. customgradually warms to room temperature
  3. stirringis stirred overnight
  4. additionTo this solution is added aqueous HCl (1 M) and ethyl acetate
  5. customThe layers are separated
  6. washthe organic portion is washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-4396593bd6f14b1181c32e54f53dcc04
출처 데이터셋
uspto-grants-2000_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06037361

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