Imidazole → HCID 58844716, compound

HRID 1271114Notes

Reaction equation

HRID 1271114 reaction equation
[OH:1][CH2:2][C:3]1[S:7][C:6]([C:8](=[O:10])[CH3:9])=[CH:5][CH:4]=1.N1C=CN=C1.[C:16]([Si:20]([CH3:23])([CH3:22])Cl)([CH3:19])([CH3:18])[CH3:17]>CN(C=O)C>[Si:20]([O:1][CH2:2][C:3]1[S:7][C:6]([C:8](=[O:10])[CH3:9])=[CH:5][CH:4]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 18451718HCID 18451718, compound

Product 1

HCID 58844716HCID 58844716, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[5-(hydroxymethyl)thien-2-yl]ethanone prepared in the above step in DMF (84 ml) was added imidazole (27.11 g) and thereto was dropped under ice cooling tert-butyldimethylchlorosilane (30.01 g). Thirty minutes later, thereto was added ice water (250 ml) and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give 1-[5-({[tert-butyl(dimethyl)silyl]oxy}methyl)thien-2-yl]ethanone (46.53 g).

Workup

  1. additionwas dropped under ice
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-18c93a75b1ca43498b1443884b11c7d8
Source dataset
uspto-grants-2007_04
Patent number
US07205291B2

Reaction notes

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