Imidazole → HCID 58844716, compound

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

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).