Imidazole → HCID 86741754, compound

HRID 1789527Notes

Reaction equation

HRID 1789527 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].[Si:8](Cl)([C:11]([CH3:14])([CH3:13])[CH3:12])([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]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].[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 86741754HCID 86741754, compound

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). Imidazole (199 g, 2.91 moles) is added in one portion and the solution is stirred at room temperature for 6 hours, after which time water (1 liter) is added and the reaction 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. customthe reaction partitioned with hexanes
  2. customThe organic phase is separated
  3. dry with materialThe residue is dried over anhydrous magnesium sulfate
  4. customthe remaining solvent removed under vacuum
  5. customleaving a clear, colorless oil
  6. distillationThe crude product is subsequently fractionally distilled under reduced pressure

Sources & evidence

ORD record
ord-70d1a100986c414c97318dea1fbc40ac
Source dataset
uspto-grants-1987_08
Patent number
US04689349

Reaction notes

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