Ammonium Chloride → 1-[4-(tert-Butyldiphenylsilyloxymethyl)-1-(2-propenyl)-1H-imidazol-2-yl]ethanone

HRID 242382Notes

Reaction equation

HRID 242382 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[N:21]=[CH:22][N:23]([CH2:25][CH:26]=[CH2:27])[CH:24]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.CON(C)[C:36](=[O:38])[CH3:37].[Cl-].[NH4+]>C1COCC1>[Si:1]([O:18][CH2:19][C:20]1[N:21]=[C:22]([C:36](=[O:38])[CH3:37])[N:23]([CH2:25][CH:26]=[CH2:27])[CH:24]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 537505N-Methoxy-N-methylacetamideHCID 892621944-(tert-Butyldiphenylsilyloxymethyl)-1-(2-propenyl)-1H-imidazoleHCID 178418339Butyllithium

Product 1

HCID 892622101-[4-(tert-Butyldiphenylsilyloxymethyl)-1-(2-propenyl)-1H-imidazol-2-yl]ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

The compound (1.26 g) obtained in (1) was dissolved in THF (50 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, 1.82 mL), followed by stirring at the same temperature for 30 minutes. Then, N-methoxy-N-methylacetamide (1.05 mL) was added, and stirring was continued for 30 minutes. 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=5%→70%) using silica gel column (product name: Hi-Flash Column 3 L, manufactured by Yamazen Corporation) to afford the title compound (0.75 g).

Workup

  1. stirringby stirring at the same temperature for 30 minutes
  2. stirringstirring
  3. customto terminate
  4. customthe reaction
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationsubsequently the solvent was distilled off under reduced pressure
  9. customThe resulting residue was purified by flash chromatography (ethyl acetate/hexane=5%→70%)

Sources & evidence

ORD record
ord-4470891a37844a9a996a6b0a55a1f76c
Source dataset
uspto-grants-2014_02
Patent number
US08653126B2

Reaction notes

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