Imidazole → HCID 123667565, compound

HRID 716151Notes

Reaction equation

HRID 716151 reaction equation
[CH:1]([Si:4](Cl)([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[C:12]1([CH:18]([CH:22]([OH:24])[CH3:23])[CH2:19][CH2:20][OH:21])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1C=CN=C1.C(OCC)(=O)C>CN(C)C=O.O>[C:12]1([CH:18]([CH2:19][CH2:20][O:21][Si:4]([CH:8]([CH3:10])[CH3:9])([CH:5]([CH3:7])[CH3:6])[CH:1]([CH3:3])[CH3:2])[CH:22]([OH:24])[CH3:23])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 139400Triisopropylsilyl chlorideHCID 89975555HCID 89975555, compound

Product 1

HCID 123667565HCID 123667565, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1.25 mL of triisopropylsilyl chloride was added dropwise to a solution of 1.0 g of 3-phenylpentane-1,4-diol and 0.45 g of imidazole in 20 mL of N,N-dimethylformamide in a nitrogen atmosphere at a temperature of 5° C. to 10° C., and the obtained mixture was then stirred at room temperature for 19 hours. Thereafter, ethyl acetate and water were added to the reaction mixture. The organic layer was fractionated, and it was washed with a saturated sodium chloride aqueous solution and was then dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/19 to 1/10), so as to obtain 1.2 g of 3-phenyl-5-((tris(propan-2-yl)silyl)oxy)pentan-2-ol in the form of a colorless oily product.

Workup

  1. washit was washed with a saturated sodium chloride aqueous solution
  2. dry with materialwas then dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled away under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/19 to 1/10)

Sources & evidence

ORD record
ord-ee5294f9cd6146198011302c6000363f
Source dataset
uspto-grants-2015_11
Patent number
US09187514B2

Reaction notes

Loading…