Water → t-Butyl[(4-ethynyl-2-thienyl)methoxy]dimethylsilane

To a solution of (4-ethynyl-2-thienyl)methanol (0.88 g, 6.4 mmol) that was obtained in Example 9 (9c) in dichloromethane (20 ml) were added successively triethylamine (1.3 ml, 9.6 mmol), t-butyldimethylchlorosilane (1.2 g, 7.6 mmol), and 4-dimethylaminopyridine (78 mg, 0.64 mmol) with stirring, and the resulting mixture was stirred at room temperature for 1 hour. After stirring, water (50 ml) was added to the reaction mixture, and the resulting mixture was extracted with dichloromethane. 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 (0:1 to 1:9) as the eluent to afford the title compound (1.5 g) in a yield of 94% as a brown oily product.

1. stirringthe resulting mixture was stirred at room temperature for 1 hour
2. stirringAfter stirring
3. extractionthe resulting mixture was extracted with dichloromethane
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-b76f928c653945f384537750d898d9e7

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07687491B2