Imidazole → tert-Butyl(4-chlorobutoxy)dimethylsilane

HRID 2170991Notes

Reaction equation

HRID 2170991 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6].N1C=CN=C1.[CH3:12][C:13]([Si:16](Cl)([CH3:18])[CH3:17])([CH3:15])[CH3:14]>C(Cl)Cl>[C:13]([Si:16]([O:6][CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])([CH3:18])[CH3:17])([CH3:15])([CH3:14])[CH3:12]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 135694-Chloro-1-butanolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 3382519tert-Butyl(4-chlorobutoxy)dimethylsilaneYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 7-a, 4-chloro-1-butanol, (CAS 928-51-8) (100 g, 920 mmol) was dissolved in CH2Cl2 (1000 mL) at room temperature. Imidazole (CAS 288-32-4) (81.5, 1200 mmol) and TBDMS-Cl (CAS 18162-48-6) (152 g, 1010 mmol) was added at 0° C. The mixture was stirred for 4 h at rt. The mixture was filtered off. The filtrate was washed with 10% aqueous HCl-solution and brine. After evaporation of the filtrate, we get the product 7-c as a clear oil (100 g, 50%).

Workup

  1. filtrationThe mixture was filtered off
  2. washThe filtrate was washed with 10% aqueous HCl-solution and brine
  3. customAfter evaporation of the filtrate, we

Sources & evidence

ORD record
ord-01a49347e2b446a5ad884f4b70f95fe2
Source dataset
uspto-grants-2015_06
Patent number
US09051317B2

Reaction notes

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