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

HRID 1436142Notes

Reaction equation

HRID 1436142 reaction equation
[C:1]([Si:5]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)Cl)([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[Br:24][CH2:25][C@H:26]([CH3:29])[CH2:27][OH:28].O>C1COCC1>[Br:24][CH2:25][C@H:26]([CH3:29])[CH2:27][O:28][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 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 8028TetrahydrofuranSolvent

Procedure

tert-Butyldiphenylchlorosilane (83 mL) and imidazole (30 g) were added to a solution of (R)-3-bromo-2-methyl-1-propanol (45 g) in THF (150 mL) under ice-cooling, and the reaction mixture was stirred at room temperature overnight. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane-ethyl acetate system) to obtain 117 g of the title compound. The property values of the compound are as follows.

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-52b61b7268384981a099ffc3bb22d10b
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Reaction notes

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