Water → HCID 68523939, Verbindung

To a solution of 4,5,6,7-tetrahydro-1-benzothien-4-yl acetate (5.1 g, 26 mmol) in chloroform (30 ml) was added N-bromosuccinimide (5 g, 28 mmol) at 0° C. with stirring, and the resulting mixture was stirred at room temperature for 3 hours. After stirring, the reaction mixture was poured into water (40 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. Subsequently, to a solution of the residue thus obtained in a mixed solvent of tetrahydrofuran (20 ml) and water (20 ml) was added sodium hydroxide (2.3 g, 57 mmol) with stirring, and the resulting mixture was stirred for 2 hours. After stirring, the reaction mixture was poured into water (50 ml) to quench the reaction 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 (3:7) as the eluent to afford the title compound (5.0 g) in a yield of 82% as a colourless oily product.

1. stirringthe resulting mixture was stirred at room temperature for 3 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
8. customSubsequently, to a solution of the residue thus obtained in a mixed solvent of tetrahydrofuran (20 ml) and water (20 ml)
9. stirringwith stirring
10. stirringthe resulting mixture was stirred for 2 hours
11. stirringAfter stirring
12. customto quench
13. customthe reaction
14. extractionextracted with ether
15. washThe extract was washed with a saturated aqueous solution of sodium chloride
16. dry with materialdried over magnesium sulfate
17. filtrationAfter filtration
18. customthe filtrate was evaporated in vacuo

ORD-Eintrag

ord-5789fb05c91c4efba76d900398bb2533

Quelldatensatz

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07687491B2