Imidazole → HCID 11391885, compound

HRID 2409421Notes

Reaction equation

HRID 2409421 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([CH2:8][CH2:9][OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].N1C=CN=C1>O1CCCC1>[C:16]([Si:13]([CH3:15])([CH3:14])[O:10][CH2:9][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=1)([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 74944-Nitrophenethyl alcoholHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 11391885HCID 11391885, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-nitrophenethylalcohol (1.0 g, 5.98 mmol) was dissolved in tetrahydrofuran (20 ml), sequentially added with t-butyldimethylsilyl chloride (990 mg, 6.58 mmol) and imidazole (450 mg, 6.58 mmol). The resulting mixture was stirred for one day and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated to dryness. The residue was then purified by flash column chromatography (ethylacetate:hexane=1:8) to obtain the title compound (1.65 g, yield: 98%, yellow oil).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated to dryness
  5. customThe residue was then purified by flash column chromatography (ethylacetate:hexane=1:8)

Sources & evidence

ORD record
ord-a40ccc0e2e8643449ae08ab29d1790d8
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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