Imidazole → 3-(2-((Triisopropylsilyl)oxy)ethyl)benzaldehyde

HRID 41138Notes

Reaction equation

HRID 41138 reaction equation
Cl[Si:2]([CH:9]([CH3:11])[CH3:10])([CH:6]([CH3:8])[CH3:7])[CH:3]([CH3:5])[CH3:4].[OH:12][CH2:13][CH2:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[O:19].N1C=CN=C1>CN(C)C=O.O>[CH:3]([Si:2]([CH:9]([CH3:11])[CH3:10])([CH:6]([CH3:8])[CH3:7])[O:12][CH2:13][CH2:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[O:19])([CH3:5])[CH3:4]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 184247323-(2-Hydroxyethyl)benzaldehyde

Product 1

HCID 547576553-(2-((Triisopropylsilyl)oxy)ethyl)benzaldehydeYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Chlorotriisopropylsilane (0.640 g, 0.71 mL, 3.3 mmol) was added dropwise to a 0° C. cooled solution of 13 (0.450 g, 3.0 mmol) and 1H-imidazole (0.410 g, 6.0 mmol) in anhydrous N,N-dimethylformamide (10 mL). The reaction mixture was stirred at 0° C. for 3 h and then diluted with water. The resulting mixture was extracted with diethyl ether, and the combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified by silica gel column chromatography using ethyl acetate-hexanes 1:9 as eluent to furnish the desired compound as colorless oil. Yield: 96%.

Workup

  1. extractionThe resulting mixture was extracted with diethyl ether
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-012aadcc994d48c0a6ed9bc397ef13bb
Source dataset
uspto-grants-2013_09
Patent number
US08530520B2

Reaction notes

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