Water → (4-Ethynyl-2-thienyl)methanol

Temperature

0 °C

To a solution of 4-ethynylthiophene-2-carboxaldehyde (1.5 g, 11 mmol) that was obtained in Example 9 (9b) in methanol (30 ml) was added sodium borohydride (0.49 g, 13 mmol) at 0° C. with stirring, and then the resulting mixture was stirred at room temperature for 15 minutes. After cooling the reaction mixture to 0° C., water (100 ml) was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. 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 (1:9 to 3:7) as the eluent to afford the title compound (0.88 g) in a yield of 60% as a brown oily product.

1. stirringthe resulting mixture was stirred at room temperature for 15 minutes
2. extractionthe resulting mixture was extracted with ethyl acetate
3. washThe extract was washed with a saturated aqueous solution of sodium chloride
4. dry with materialdried over magnesium sulfate
5. filtrationAfter filtration
6. customthe filtrate was evaporated in vacuo

ORD record

ord-3f3295ce5b63415db99afff402aa9ad7

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07687491B2