Imidazole → ((3-Bromonaphthalen-1-yl)methoxy)triisopropylsilane

HRID 46223Notes

Reaction equation

HRID 46223 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:12][OH:13])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.N1C=CN=C1.[CH3:19][CH:20]([Si:22](Cl)([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[CH3:21]>CN(C=O)C.CN(C1C=CN=CC=1)C.[Cl-].[NH4+]>[Br:1][C:2]1[CH:3]=[C:4]([CH2:12][O:13][Si:22]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:21])[CH3:19])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

7

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 12749165(3-Bromonaphthalen-1-yl)methanol

Product 1

HCID 59463745((3-Bromonaphthalen-1-yl)methoxy)triisopropylsilaneYield 96%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of (3-bromonaphthalen-1-yl)methanol in DMF (100 mL) was added imidazole (6.4 g, 93 mmol), DMAP (0.57 g, 4.7 mmol), and TIPSCl (15 mL, 70 mmol). The resulting solution was stirred at room temperature for 12 h, diluted with a saturated ammonium chloride and extracted with EtOAc. The organic layer was washed with water then brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The crude residue was purified by column chromatography (3-10% EtOAc/hexanes) to yield the title compound (17.9 g, 96%) as a colorless oil.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water
  3. dry with materialbrine, dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by column chromatography (3-10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-3270066dc9494738a1fed70eb9f13b4f
Source dataset
uspto-grants-2013_09
Patent number
US08541380B2

Reaction notes

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