Imidazole → HCID 20519039, 화합물

HRID 1644215노트

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HRID 1644215 반응식
N1C=CN=C1.[Br:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([OH:17])=[CH:9][CH:8]=1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>CN(C=O)C>[Br:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])=[CH:9][CH:8]=1

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 5756094-Bromonaphthalen-1-ol

생성물 1

HCID 20519039HCID 20519039, 화합물수율 86.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of imidazole (2.3 g, 34 mmole) and 4-bromonaphthol (13, 5.0 g, 22 mmole) in DMF (10 mL) at 0° C. was added t-butyldimethylsilyl chloride (3.7 g, 24.6 mmole) in several portions. The mixture was warmed to room temperature and stirred for 2 h. The reaction mixture was partitioned between Et2O (500 mL) and water (300 mL) and the aqueous layer was back-extracted with Et2O (300 mL). The combined organic layers were washed with water (300 mL) and brine (300 mL), dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography (silica gel, hexanes) to afford (4-bromonaphthalen-1-yloxy)(tert-butyl)dimethylsilane (14, 6.4 g, 85%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 8.21 8.14 (m, 2H), 7.61-7.49 (m, 3H), 6.74 (d, J=8.2 Hz, 1H), 1.10 (s, 9H), 0.28 (s, 6H).

후처리

  1. customThe reaction mixture was partitioned between Et2O (500 mL) and water (300 mL)
  2. extractionthe aqueous layer was back-extracted with Et2O (300 mL)
  3. washThe combined organic layers were washed with water (300 mL) and brine (300 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (silica gel, hexanes)

출처 및 근거

ORD 기록
ord-a8d4ed57a9bc4790b560056c943de546
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124607B2

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