Imidazole → HCID 11077853, compound

HRID 538908Notes

Reaction equation

HRID 538908 reaction equation
N1C=CN=C1.[CH2:6]1[O:8][C@@H:7]1[CH2:9][OH:10].[CH3:11][C:12]([Si:15](Cl)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:14])[CH3:13]>CN(C=O)C>[C:12]([Si:15]([O:10][CH2:9][C@@H:7]1[CH2:6][O:8]1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([CH3:14])([CH3:11])[CH3:13]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 5460455(+)-Glycidol

Product 1

HCID 11077853HCID 11077853, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (6.6 g, 97.2 mmol) and DMF (75 ml) were added to (R)-glycidol (2.7 ml, 40.5 mmol) (13a), and the resulting mixture was stirred. Then, TBDPSCl (12.6 ml, 48.6 mmol) was added and reacted at 0° C. overnight. Next day, after disappearance of the spots of the raw material was observed by thin-layer chromatography (TLC) (hereinafter referred to as TLC), the product was extracted with ethyl acetate and distilled water, to recover an organic layer. The organic layer was washed with saturated sodium hydrogen carbonate and a saturated salt solution, and dried with anhydrous sodium sulfate. The solvent was evaporated using a vacuum evaporator, and the residue was isolated and purified by silica gel column chromatography (hexane:ethyl acetate=50:1). Thus, a compound (13b) (S)-tert-butyl(oxiran-2-ylmethoxy)diphenylsilane (4.5664 g, 15 mmol, 37%) was obtained as a colorless and transparent liquid.

Workup

  1. customreacted at 0° C. overnight
  2. extractionwas extracted with ethyl acetate
  3. distillationdistilled water
  4. customto recover an organic layer
  5. washThe organic layer was washed with saturated sodium hydrogen carbonate
  6. dry with materiala saturated salt solution, and dried with anhydrous sodium sulfate
  7. customThe solvent was evaporated
  8. customa vacuum evaporator
  9. customthe residue was isolated
  10. custompurified by silica gel column chromatography (hexane:ethyl acetate=50:1)

Sources & evidence

ORD record
ord-76e62ab2b113416ea6ef915ca88725b9
Source dataset
uspto-grants-2014_10
Patent number
US08865898B2

Reaction notes

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