Imidazole → tert-Butyl(5-ethyl-2-fluorophenoxy)dimethylsilane

HRID 1698741Notes

Reaction equation

HRID 1698741 reaction equation
N1C=CN=C1.[C:6]([Si:10]([CH3:13])([CH3:12])Cl)([CH3:9])([CH3:8])[CH3:7].[CH2:14]([C:16]1[CH:17]=[CH:18][C:19]([F:23])=[C:20]([OH:22])[CH:21]=1)[CH3:15].C(OCC)C>CN(C=O)C.O>[C:6]([Si:10]([O:22][C:20]1[CH:21]=[C:16]([CH2:14][CH3:15])[CH:17]=[CH:18][C:19]=1[F:23])([CH3:13])[CH3:12])([CH3:9])([CH3:8])[CH3:7]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 28928tert-Butyldimethylsilyl chlorideHCID 187116495-Ethyl-2-fluorophenol

Product 1

HCID 59838026tert-Butyl(5-ethyl-2-fluorophenoxy)dimethylsilaneYield 85.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

After adding 9.16 g of imidazole and 19.4 g of t-butyldimethylchlorosilane to a solution of 16.4 g of 5-ethyl-2-fluorophenol in 40 ml of DMF, the reaction mixture was stirred at room temperature for 18 hours. After then adding 500 ml of diethyl ether and 500 ml of water to the reaction mixture, the organic layer was washed twice with 100 ml of water and once with 100 ml of saturated aqueous sodium chloride in that order and then dried over anhydrous magnesium sulfate, the desiccating agent was filtered off, and the filtrate was concentrated under reduced pressure. The residue was subjected to distillation to give the title compound (25.38 g) as a colorless liquid (boiling point: 133-135° C., 20 mmHg).

Workup

  1. washthe organic layer was washed twice with 100 ml of water and once with 100 ml of saturated aqueous sodium chloride in that order
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationthe desiccating agent was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. distillationThe residue was subjected to distillation

Sources & evidence

ORD record
ord-70d0c557a6cc4ec6a87c6cbdd2ad21dc
Source dataset
uspto-grants-2012_04
Patent number
US08163787B2

Reaction notes

Loading…