Imidazole → HCID 123241194, compound

HRID 1055166Notes

Reaction equation

HRID 1055166 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][C@H:25]1[CH2:27][OH:28]>C(#N)C>[Si:10]([O:28][CH2:27][C@H: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 94078tert-ButyldiphenylchlorosilaneHCID 6973630(-)-Glycidol

Product 1

HCID 123241194HCID 123241194, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Add 1H-imidazole (14.70 g; 4 equiv; 215.99 mmoles) followed by tert-butylchlorodiphenylsilane (14.00 mL; 1.0 equiv; 54.00 mmoles) to a 0° C. solution of freshly distilled (S)-glycidol (3.66 mL; 1.0 equiv; 54.00 mmoles) in acetonitrile (40 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 and 2M sodium bicarbonate solution (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 (2R)-1-[tert-butyl(diphenyl)silyl]oxy-3-imidazol-1-yl-propan-2-ol (9.25 g; 45%). 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 and 2M sodium bicarbonate solution (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-2e7ff827de134b18bcf64800d21bd9f8
Source dataset
uspto-grants-2016_07
Patent number
US09394317B2

Reaction notes

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