Imidazole → HCID 15159186, compound

HRID 1613151Notes

Reaction equation

HRID 1613151 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.[Si:8]([O:15][CH2:16][CH2:17]Br)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]>CN(C=O)C>[Si:8]([O:15][CH2:16][CH2:17][N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Product 1

HCID 15159186HCID 15159186, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To 86.4 mg (2.2 mmoles) of 61.1% sodium hydride mineral oil dispersion in 5 mL sieve dried DMF at 0° C. was added 136 mg (2.0 mmoles) of imidazole. The mixture was stirred at 0° C. under nitrogen for 15 minutes and 476 mg (2.0 mmoles) of neat t-butyldimethylsilyloxyethyl bromide was added. The ice-water bath was removed and the mixture stirred overnight and it was then partitioned between ether and ice-water. The organic phase was separated, washed thrice with ice-water, dried over sodium sulfate, filtered, and evaporated to give 282.3 mg (63%) of the title compound.

Workup

  1. customThe ice-water bath was removed
  2. stirringthe mixture stirred overnight
  3. customit was then partitioned between ether and ice-water
  4. customThe organic phase was separated
  5. washwashed thrice with ice-water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-b223883a33e44afe9540a333b0416184
Source dataset
uspto-grants-1993_03
Patent number
US05192758

Reaction notes

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