Ammonium Chloride → HCID 89262250, compound

HRID 242379Notes

Reaction equation

HRID 242379 reaction equation
[Si](OCC1N=CN(CCF)C=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[Si:28]([O:45][CH2:46][C:47]1[N:51]([CH2:52][CH2:53]F)[CH:50]=[N:49][CH:48]=1)([C:41]([CH3:44])([CH3:43])[CH3:42])([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([Li])CCC.[Cl-].[NH4+]>C1COCC1>[Si:28]([O:45][CH2:46][C:47]1[N:51]([CH:52]=[CH2:53])[CH:50]=[N:49][CH:48]=1)([C:41]([CH3:44])([CH3:42])[CH3:43])([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 71087269HCID 71087269, compoundHCID 71087378HCID 71087378, compoundHCID 178418339Butyllithium

Product 1

HCID 89262250HCID 89262250, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

The above-mentioned mixture (58.87 g) of 4-(tert-butyldiphenylsilyloxymethyl)-1-(2-fluoroethyl)-1H-imidazole and 5-(tert-butyldiphenylsilyloxymethyl)-1-(2-fluoroethyl)-1H-imidazole was dissolved in THF (1000 mL), and cooled to −78° C. while stirring under nitrogen stream. To the present solution was added dropwise n-butyl lithium (2.76 M hexane solution, 167 mL), followed by stirring at the same temperature for 1 hour. A saturated aqueous ammonium chloride solution was added to the reaction solution to terminate the reaction, followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and subsequently the solvent was distilled off under reduced pressure. The resulting residue was purified by flash chromatography (ethyl acetate/hexane=10%→65%) using silica gel column (product name: KiloPack 40E, manufactured by Yamazen Corporation) to afford the title compound (18.8 g) and 5-(tert-butyldiphenylsilyloxymethyl)-1-vinyl-1H-imidazole (5.73 g).

Workup

  1. stirringby stirring at the same temperature for 1 hour
  2. customto terminate
  3. customthe reaction
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationsubsequently the solvent was distilled off under reduced pressure
  8. customThe resulting residue was purified by flash chromatography (ethyl acetate/hexane=10%→65%)

Sources & evidence

ORD record
ord-a4ab6b464fb14aada17da2999b7eb84a
Source dataset
uspto-grants-2014_02
Patent number
US08653126B2

Reaction notes

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