Imidazole → Silane, [(3-bromo-3-butenyl)oxy](1,1-dimethylethyl)dimethyl-

HRID 627279Notes

Reaction equation

HRID 627279 reaction equation
[Br:1][C:2](=[CH2:6])[CH2:3][CH2:4][OH:5].N1C=CN=C1.[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Br:1][C:2](=[CH2:6])[CH2:3][CH2:4][O:5][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 5339753-Bromo-3-buten-1-ol

Product 1

HCID 11129203Silane, [(3-bromo-3-butenyl)oxy](1,1-dimethylethyl)dimethyl-Yield 93%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromobut-3-en-1-ol (ACROS, 15.18 g, 100.53 mmol) in DCM (300 mL) at room temperature was added imidazole (8.90 g, 130.69 mmol), 4-dimethylaminopyridine (2.456 g, 20.11 mmol) and tert-butyldimethylsilyl chloride (16.67 g, 110.58 mmol). The reaction mixture was stirred at room temperature for 3 hours, then filtered to remove solids and washed with brine. The organics were dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (0%-15% ethyl acetate/hexanes) afforded the title compound (24.67 g, 93%) as a colorless oil.

Workup

  1. filtrationfiltered
  2. customto remove solids
  3. washwashed with brine
  4. dry with materialThe organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-25ec1eff87b54ffc957ebbe066fb6d95
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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