Imidazole → 2-[(tert-butyldimethylsilyloxy)methyl]benzylalcohol

HRID 578799Notes

Reaction equation

HRID 578799 reaction equation
[C:1]1([CH2:9][OH:10])[C:2]([CH2:7][OH:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.N1C=CN=C1.[C:16]([Si:20]([CH3:23])([CH3:22])Cl)([CH3:19])([CH3:18])[CH3:17]>CN(C)C=O.C(OCC)(=O)C>[Si:20]([O:8][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH2:9][OH:10])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 691531,2-Benzenedimethanol

Product 1

HCID 108484452-[(tert-butyldimethylsilyloxy)methyl]benzylalcoholYield 41.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,2-benzenedimethanol (2 g) and imidazole (1.13 g) in N,N-dimethylformamide (30 mL) was added tert -butyldimethylchlorosilane (2.08 g), and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with ethyl acetate, and the resulting mixture was washed with 1 mol/L hydrochloric acid, water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=3/2) to give the title compound (1.46 g).

Workup

  1. washthe resulting mixture was washed with 1 mol/L hydrochloric acid, water and brine successively
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=3/2)

Sources & evidence

ORD record
ord-42fc0e5b916744c58986e36b2fa15a33
Source dataset
uspto-grants-2015_05
Patent number
US09040693B2

Reaction notes

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