Imidazole → Tert-butyl(2-(2-chloroethoxy)ethoxy)dimethylsilane

HRID 1030551Notes

Reaction equation

HRID 1030551 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[Cl:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][OH:20].[Na+].[Cl-]>CN(C)C=O>[Cl:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 5234Sodium ChlorideHCID 123612-(Chloroethoxy)ethanolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 4555750Tert-butyl(2-(2-chloroethoxy)ethoxy)dimethylsilaneYield 100.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (17.8 g, 261 mmol) was dissolved in dimethylformamide (100 ml) and t-butyldimethylsilyl chloride (36.3 g, 241 mmol) was added and stirred. 2-(2-chloroethoxy)ethanol (25.0 g, 200 mmol) was added dropwise over 1 hour under cooling with ice, and the mixture was stirred for 1 further hour, left standing overnight at room temperature, and then poured into saturated aqueous NaCl (500 ml). The resulting mixture was extracted twice with ether. The extract was washed twice with saturated aqueous NaCl, and dried over MgSO4. Then the solvent was removed in vacuo, giving 1-chloro-2-(2-t-butyldimethylsilyloxyethoxy)ethane (47.8 g, 100% yield). IR (CHCl3) [cm-1 ]; 2920, 2850, 1460, 1100, 930. NMR (CDCl3) [δ ppm]; 3.94-3.90 (4 H, m) 3.79-3.72 (4 H, m), 1.05 (9 H, s), 0.22 (6 H, s).

Workup

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred for 1 further hour
  3. waitleft
  4. extractionThe resulting mixture was extracted twice with ether
  5. washThe extract was washed twice with saturated aqueous NaCl
  6. dry with materialdried over MgSO4
  7. customThen the solvent was removed in vacuo

Sources & evidence

ORD record
ord-7504211e68ba4080a977dcf0ae49d6ea
Source dataset
uspto-grants-1992_04
Patent number
US05106860

Reaction notes

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