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Imidazole → HCID 18536138, 화합물

HRID 412184
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HRID 412184 반응식
[I:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([OH:12])[CH:8]=[CH:7]2.N1C=CN=C1.[CH:18]([Si:21](Cl)([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])([CH3:20])[CH3:19]>CN(C=O)C>[CH:18]([Si:21]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[O:12][C:9]1[CH:10]=[C:11]2[C:6]([CH:5]=[CH:4][CH:3]=[C:2]2[I:1])=[CH:7][CH:8]=1)([CH3:20])[CH3:19]
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참가 물질

5

반응물 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 6229868-Iodo-2-naphthol

생성물 1

HCID 18536138HCID 18536138, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 8-iodo-2-naphthol, as described in Step A of Example 103 (2.75 g, 10.2 mmol) in dry DMF (25 mL), under argon, were added imidazole (1.39 g, 20.4 mmol) and triisopropylsilyl chloride (2.55 g, 13.2 mmol). The resulting mixture was stirred at ambient temperature for 4 hrs, then quenched with 10% aqueous citric acid (100 mL) and extracted with EtOAc (2×100 mL). The combined organic extracts were washed with water (50 mL), then brine (50 mL), then dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with CH2Cl2—50% hexane to yield the desired product as a white solid.

후처리

  1. customquenched with 10% aqueous citric acid (100 mL)
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe combined organic extracts were washed with water (50 mL)
  4. dry with materialbrine (50 mL), then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica
  8. washeluting with CH2Cl2—50% hexane

출처 및 근거

ORD 기록
ord-ba6268baaacd42cc88dfad742fc756e4
출처 데이터셋
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06562823B1

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