Imidazole → ((R)-3-bromo-2-methylpropoxy)-tert-butyldiphenylsilane

HRID 1026568Notes

Reaction equation

HRID 1026568 reaction equation
[Br:1][CH2:2][C@H:3]([CH3:6])[CH2:4][OH:5].N1C=CN=C1.[C:12]([Si:16](Cl)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:15])([CH3:14])[CH3:13].[Cl-].[NH4+]>CN(C)C=O>[Br:1][CH2:2][C@H:3]([CH3:6])[CH2:4][O:5][Si:16]([C:12]([CH3:15])([CH3:14])[CH3:13])([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 94078tert-ButyldiphenylchlorosilaneHCID 10441885(R)-(-)-3-Bromo-2-methyl-1-propanol

Product 1

HCID 69007455((R)-3-bromo-2-methylpropoxy)-tert-butyldiphenylsilane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an N,N-dimethylformamide solution (50.0 ml) of (2R)-3-bromo-2-methyl-1-propanol (7.63 g) were added under ice cooling imidazole (7.13 g) and tert-butylchlorodiphenylsilane (14.8 ml), followed by stirring at room temperature for 5 hours. The reaction solution was poured into a saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography to afford {[(2R)-3-bromo-2-methylpropyl]oxy}(tert-butyl)diphenylsilane (19.2 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-613205832af54b7590d809b4f5e51f6e
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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