Imidazole → (5-Chloro-1-pentyloxy)(2,2-dimethylethyl)dimethylsilane

HRID 1722366Notes

Reaction equation

HRID 1722366 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].[Si:8](Cl)([C:11](C)(C)C)([CH3:10])[CH3:9].[CH3:16]N(C)C=O.N1[CH:25]=[CH:24]N=C1>O>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][Si:8]([CH2:11][CH:24]([CH3:25])[CH3:16])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 789155-Chloro-1-pentanol

Product 1

HCID 20028701(5-Chloro-1-pentyloxy)(2,2-dimethylethyl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Chloropentanol (325 g, 2.65 moles) is added to a solution containing tert-butyldimethylsilyl chloride (439 g, 2.91 moles) and dimethylformamide (1.625 liters). The solution is stirred and imidazole (199 g, 2.91 moles) is added at once. The solution is stirred at room temperature for 6 hours, after which time water (1 liter) is added and the reaction is partitioned with hexanes. The organic phase is separated and the solvent volume reduced under vacuum. The residue is dried over anhydrous magnesium sulfate and the remaining solvent removed under vacuum, leaving a clear, colorless oil. The crude product is subsequently fractionally distilled under reduced pressure leaving the product as a clear, colorless oil (534 g, 2.26 moles), BP 71° C./0.3 mm.

Workup

  1. stirringThe solution is stirred at room temperature for 6 hours
  2. customthe reaction is partitioned with hexanes
  3. customThe organic phase is separated
  4. dry with materialThe residue is dried over anhydrous magnesium sulfate
  5. customthe remaining solvent removed under vacuum
  6. customleaving a clear, colorless oil
  7. distillationThe crude product is subsequently fractionally distilled under reduced pressure

Sources & evidence

ORD record
ord-ec93d5375f7b4828b6fa9483421a2b2a
Source dataset
uspto-grants-1989_08
Patent number
US04855322

Reaction notes

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