Imidazole → HCID 90424727, compound

HRID 1055161Notes

Reaction equation

HRID 1055161 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[C:6]([Si:10](Cl)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:9])([CH3:8])[CH3:7].[CH2:24]1[O:26][CH:25]1[CH2:27][OH:28]>C(#N)C>[Si:10]([O:28][CH2:27][CH:25]([OH:26])[CH2:24][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)([C:6]([CH3:9])([CH3:8])[CH3:7])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11164GlycidolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 90424727HCID 90424727, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Add 1H-imidazole (19.72 g; 6.2 equiv; 289.67 mmoles) followed by tert-butylchlorodiphenylsilane (12.00 mL; 1.0 equiv; 46.28 mmoles) to a solution of freshly distilled glycidol (5.0 mL; 1.62 equiv; 75.05 mmoles) in acetonitrile (50 mL). Stir the solution at ambient temperature for 30 minutes, then heat to reflux for 4 hours. Allow the mixture to cool to ambient temperature and concentrate the reaction mixture, then pour the residue into dichloromethane/2M sodium bicarbonate (1:1, 400 mL). Separate the layers and further extract the aqueous layer with dichloromethane (2×). Dry the combined organic extracts over magnesium sulfate, filter, and concentrate to afford crude product. Purification by column chromatography affords the desired 1-[tert-butyl(diphenyl)silyl]oxy-3-imidazol-1-yl-propan-2-ol (8.87 g; 50%). MS (m/z): 381(M+1).

Workup

  1. temperatureheat
  2. temperatureto reflux for 4 hours
  3. temperatureAllow the mixture to cool to ambient temperature
  4. concentrationconcentrate the reaction mixture
  5. additionpour the residue into dichloromethane/2M sodium bicarbonate (1:1, 400 mL)
  6. customSeparate the layers
  7. extractionfurther extract the aqueous layer with dichloromethane (2×)
  8. dry with materialDry the combined organic extracts over magnesium sulfate
  9. filtrationfilter
  10. concentrationconcentrate
  11. customto afford crude product
  12. customPurification by column chromatography

Sources & evidence

ORD record
ord-a99c9ac02efe40a285a48b3c0a838a8a
Source dataset
uspto-grants-2016_07
Patent number
US09394317B2

Reaction notes

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