Imidazole → [4-(3-Bromophenyl)butoxy](tert-butyl)diphenylsilane

HRID 916841Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 916841
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][CH:7]=1.N1C=CN=C1.[Si:18](Cl)([C:31]([CH3:34])([CH3:33])[CH3:32])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][O:12][Si:18]([C:31]([CH3:34])([CH3:33])[CH3:32])([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 218954894-(3-Bromophenyl)butan-1-ol

Produkt 1

HCID 69439190[4-(3-Bromophenyl)butoxy](tert-butyl)diphenylsilane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4-(3-bromophenyl)butan-1-ol (5 g) (WO 0266422 A1) in dry DMF was treated with imidazole (1.8 g) and tert-butyldiphenylsilyl chloride (7.2 g) and stirred at room temperature for 16 h. The reaction mixture was partitioned between water and EtOAc. The organic phase was washed with 2M HCl, water, sat. NH4Cl(aq), water, dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography (SPE, Gradient between cyclohexane and cyclohexane-EtOAc (5:1) to give the title compound. LCMS RT=4.82 min

Aufarbeitung

  1. customThe reaction mixture was partitioned between water and EtOAc
  2. washThe organic phase was washed with 2M HCl, water, sat. NH4Cl(aq), water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (SPE, Gradient between cyclohexane and cyclohexane-EtOAc (5:1)

Quellen und Nachweise

ORD-Eintrag
ord-d89f6722d1e44d8db50bb40007166e13
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07271197B2

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