Imidazole → 2-(3-(2-((Triisopropylsilyl)oxy)ethyl)phenyl)ethanol

HRID 41149Notes

Reaction equation

HRID 41149 reaction equation
[C:1]1([CH2:10][CH2:11][OH:12])[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][OH:9])[CH:2]=1.N1C=CN=C1.Cl[Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21]>CN(C)C=O.O>[CH:20]([Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[O:12][CH2:11][CH2:10][C:1]1[CH:2]=[C:3]([CH2:7][CH2:8][OH:9])[CH:4]=[CH:5][CH:6]=1)([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 100807412-[3-(2-Hydroxyethyl)phenyl]ethanol

Product 1

HCID 547578682-(3-(2-((Triisopropylsilyl)oxy)ethyl)phenyl)ethanolYield 35%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

2,2′-(1,3-Phenylene)diethanol (0.430 g, 2.59 mmol) and imidazole (0.176 g, 2.59 mmol) were dissolved in anhydrous N,N-dimethylformamide (15 mL) and cooled to 0° C. in an ice bath. Chlorotriisopropylsilane (0.22 mL) was slowly added and the reaction mixture was kept stirring at 0° C. for 3 h, and then diluted with water (5 mL), extracted with ethyl acetate (15 mL×2), and washed with brine (10 mL×2). The organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated to dryness. The residue so obtained was purified by column chromatography eluting with 1:10 of ethyl acetate-hexanes to give the desired compound as a colorless oil. Yield 35%.

Workup

  1. extractionextracted with ethyl acetate (15 mL×2)
  2. washwashed with brine (10 mL×2)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue so obtained
  7. customwas purified by column chromatography
  8. washeluting with 1:10 of ethyl acetate-hexanes

Sources & evidence

ORD record
ord-8c54f1d1436d48feb68065150aef8b89
Source dataset
uspto-grants-2013_09
Patent number
US08530520B2

Reaction notes

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