Water → 4-Ethynylthiophene-2-carbaldehyde

To a solution of 4-[(trimethylsilyl)ethynyl]thiophene-2-carboxaldehyde (3.3 g, 16 mmol) that was obtained in Example 9 (9a) in methanol (160 ml) was added potassium carbonate (4.3 g, 31 mmol) with stirring, and the resulting mixture was stirred at room temperature for 1 hour. After stirring, insoluble materials were removed by filtration, and the filtrate was evaporated in vacuo. The residue thus obtained was diluted with ethyl acetate, poured into water (100 ml) and 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 (0:1 to 1:19) as the eluent to afford the title compound (1.5 g) in a yield of 69% as a brown solid.

1. stirringthe resulting mixture was stirred at room temperature for 1 hour
2. stirringAfter stirring
3. custominsoluble materials were removed by filtration
4. customthe filtrate was evaporated in vacuo
5. customThe residue thus obtained
6. extractionextracted with ethyl acetate
7. washThe extract was washed with a saturated aqueous solution of sodium chloride
8. dry with materialdried over magnesium sulfate
9. filtrationAfter filtration
10. customthe filtrate was evaporated in vacuo

ORD record

ord-f6e6a896ad95422eb9ea3d8172dca469

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07687491B2