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Methyl iodide → HCID 19974930, 화합물

HRID 1451523
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인쇄 미리보기

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HRID 1451523 반응식
[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][CH:19]([CH3:24])[C:20]([O:22][CH3:23])=[O:21])=[C:8]2[CH3:25])=[CH:4][CH:3]=1.[Li+].[CH3:29]C([N-]C(C)C)C.IC>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][C:19]([CH3:29])([CH3:24])[C:20]([O:22][CH3:23])=[O:21])=[C:8]2[CH3:25])=[CH:4][CH:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 19974940HCID 19974940, 화합물

생성물 1

HCID 19974930HCID 19974930, 화합물수율 67.5%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 12679Hexamethylphosphoramide
용매

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온도
0 °C

실험 절차

To a -78° C. solution of the ester from Step 1 (35 mg, 0.08 mmol) in 3 mL THF was added LDA (1.5M in cyclohexane, 0.1 mL, 0.15 mmol), and the solution was stirred for 30 min. A solution of iodomethane (0.1 mL, 1.6 mmol) in 1 mL HMPA was then added by syringe. The solution was stirred 15 min at -78° C., then warmed to 0° C. and quenched with saturated NH4Cl. The mixture was partitioned between ether and water and the organic layer was washed with water and brine and dried over MgSO4. The residue was purified by flash chromatography (15% ethyl acetate/hexanes) to provide 24 mg of the title compound.

후처리

  1. stirringThe solution was stirred 15 min at -78° C.
  2. customquenched with saturated NH4Cl
  3. customThe mixture was partitioned between ether and water
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over MgSO4
  6. customThe residue was purified by flash chromatography (15% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-6d84c1163068405bbbf7679acc31daea
출처 데이터셋
uspto-grants-1997_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05604253

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