Imidazole → 1-t-Butyldiphenylsiloxy-3,5-dimethoxybenzene

HRID 1006233Notes

Reaction equation

HRID 1006233 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:11])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.N1C=CN=C1.[C:17]([Si:21](Cl)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:20])([CH3:19])[CH3:18].O>CN(C)C=O>[O:11]([C:5]1[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[Si:21]([C:17]([CH3:20])([CH3:19])[CH3:18])([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 103833,5-DimethoxyphenolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 693655901-t-Butyldiphenylsiloxy-3,5-dimethoxybenzeneYield 94.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 6.73 g (43.7 mmol) of 3,5-dimethoxyphenol in anhydrous dimethylformamide (50 mL) were added 5.95 g (87.4 mmol) of imidazole and 15.0 g (54.6 mmol) of t-butylchlorodiphenylsilane. The mixture was stirred at 50° C. for 4 hours. Water was added and the mixture was extracted with ethyl acetate-hexane (1:2). The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, whereby 16.14 g of 1-t-butyldiphenylsiloxy-3,5-dimethoxybenzene was obtained as a colorless crystalline powder (mp: 95.5 to 96.5° C., yield: 94%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate-hexane (1:2)
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f62c7403985d47e6afab4ba39b287268
Source dataset
uspto-grants-2004_09
Patent number
US06787653B2

Reaction notes

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