Imidazole → t-Butyl(dimethyl)[(4-methyl-2-thienyl)methoxy]silane

To a solution of 2-hydroxymethyl-4-methylthiophene (1.8 g, 14 mmol) (reference literature: J. Heterocycl. Chem., vol. 19, 1125 (1982)) and imidazole (1.9 g, 28 mmol) in N,N-dimethylformamide (20 ml) was added t-butyldimethylsilyl chloride (2.3 g, 15 mmol) with stirring, and the resulting mixture was stirred at room temperature for 2 hours. After stirring, the reaction mixture was poured into water (20 ml) and extracted with ether. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo, and the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (0:10 to 1:19) as the eluent to afford the title compound (2.5 g) in a yield of 74% as a colourless oily product.

1. stirringthe resulting mixture was stirred at room temperature for 2 hours
2. stirringAfter stirring
3. extractionextracted with ether
4. washThe extract was washed with a saturated aqueous solution of sodium chloride
5. dry with materialdried over magnesium sulfate
6. filtrationAfter filtration
7. customthe filtrate was evaporated in vacuo

ORD record

ord-d83df5075d254cc68b0f58f6719d2f93

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07687491B2