Imidazole → (1-Bromo-naphthalen-2-yloxy)-triisopropyl-silane

HRID 1814335

반응식

HRID 1814335 반응식
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:12].[CH:13]([Si:16](Cl)([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])([CH3:15])[CH3:14].N1C=CN=C1.N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl.O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:12][Si:16]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:13]([CH3:15])[CH3:14]

참가 물질

8

반응물 4

HCID 795ImidazoleHCID 1049PyridineHCID 113161-Bromo-2-naphtholHCID 139400Triisopropylsilyl chloride

생성물 1

HCID 22504240(1-Bromo-naphthalen-2-yloxy)-triisopropyl-silane수율 99.1%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

1-Bromo-2-naphthol (5.00 g, 22.4 mmol) was mixed with triisopropylsilyl chloride (7.2 mL, 33.6 mmol), DMAP (402 mg, 3.30 mmol), imidazole (3.81 g, 56.0 mmol), and pyridine (6 mL) in CH2Cl2 (50 mL). The reaction was refluxed for two hours. TLC analysis (silica, 15% EtOAc-hexanes) indicated the reaction was complete. The reaction was allowed to cool to room temperature and then was diluted with H2O. The dilution was extracted three times with CH2Cl2. The organic extracts were combined, washed with brine solution, dried over Na2SO4, filtered through celite, and concentrated. The crude product was purified by flash chromatography (SiO2, 100% hexanes) to give (1-bromo-naphthalen-2-yloxy)-triisopropyl-silane (8.4 g, 22.2 mmol) as a colorless oil in 99% yield. 1H NMR (300 MHz) CDCl3 8.21 (d, J=7.5 Hz, 1H), 7.76 (d, J=8.5 Hz, 1H), 7.68 (d, J=8.8 Hz, 1H), 7.54 (m, 1H), 7.38 (m, 1H), 7.15 (d, J=8.8 Hz, 1H), 1.38 (m, 3H), 1.16 (d, J=7.1 Hz, 18H).

후처리

  1. temperatureThe reaction was refluxed for two hours
  2. extractionThe dilution was extracted three times with CH2Cl2
  3. washwashed with brine solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered through celite
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography (SiO2, 100% hexanes)

출처 및 근거

ORD 기록
ord-cc6ac67d4e814cdcaac13c3e119f2ed4
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06875765B2

연결된 노트

불러오는 중…