Imidazole → HCID 19100675, compound

HRID 1975057Notes

Reaction equation

HRID 1975057 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][OH:7].N1C=CN=C1.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>CN(C=O)C>[Si:13]([O:7][CH2:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 694672-Thiophenemethanol

Product 1

HCID 19100675HCID 19100675, compoundYield 110%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A 100 ml round-bottom flask, equipped with a magnetic stirring bar, septum, and nitrogen inlet, was charged with 500 μl (3.98 mmol, 1.0 equiv) 2-thiophenemethanol and 5 ml DMF (over sieves). This clear solution was cooled down to 0° C. 825 mg (11.95 mmol, 3.0 equiv) imidazole was added in one portion, followed by the addition of 930 mg (5.97 mmol, 1.5 equiv) t-butyldimethylsilyl chloride. The reaction was kept at 0° C. for 5 minutes, warmed up to room temperature to go for half an hour, and then quenched with distilled water. Ethyl acetate was added to dissolve the organics. Layers were separated, and the aqueous layer was extracted with 5×10 ml ethyl acetate. The combined organic portion was washed with 5×20 ml H2O, dried over anhydrous sodium sulfate, filtered, concentrated, and chromatographed on a silica gel column (5 cm×24 cm, 100:1=hexane:ethyl acetate) to afford 1 gram of the title compound: Rf=0.26 (100:1=hexane:ethyl acetate), 1H NMR δ4.87 (s, OCH2), 0.91 (s, tBu), 0.09 (s, CH3).

Workup

  1. customA 100 ml round-bottom flask, equipped with a magnetic stirring bar
  2. temperaturewarmed up to room temperature
  3. waitto go for half an hour
  4. customquenched with distilled water
  5. additionEthyl acetate was added
  6. dissolutionto dissolve the organics
  7. customLayers were separated
  8. extractionthe aqueous layer was extracted with 5×10 ml ethyl acetate
  9. washThe combined organic portion was washed with 5×20 ml H2O
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customchromatographed on a silica gel column (5 cm×24 cm, 100:1=hexane:ethyl acetate)

Sources & evidence

ORD record
ord-9eaa0375605e46d7b0f21f738796b239
Source dataset
uspto-grants-1994_02
Patent number
US05284841

Reaction notes

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