2-Bromothiophene → HCID 19885898, compound

To a stirred solution of 2-bromothiophene (0.341 g, 2.09 mmol) in tetrahydrofuran (30 ml) under argon at -78° was added t-butyl lithium (2.53 ml of a 1.7M solution) followed by 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (0.268 g, 2.09 mmol). To this mixture was added 1-bromo-8-t-butyldimethylsiloxyoctane (0.615 g, 1.90 mmol in tetrahydrofuran (10 ml). After gradual warming followed by stirring at room temperature for 18 hours, the mixture was concentrated, taken up in ethyl ether and washed consecutively with cold 10% hydrochloric acid, saturated sodium bicarbonate, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give a yellow oil. To this residue in tetrahydrofuran (20 ml) at 0° was added tetrabutylammonium fluoride (8.4 ml of a 1.0M solution). After stirring for 16 hours at room temperature the mixture was concentrated, taken up in ethyl ether and washed with 10% hydrochloric acid, saturated sodium bicarbonate, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give a yellow oil. Further purification by flash chromatography (silica, 30% ethyl acetate/hexane) give the desired alcohol.

1. temperatureAfter gradual warming
2. concentrationthe mixture was concentrated
3. washwashed consecutively with cold 10% hydrochloric acid, saturated sodium bicarbonate, water, saturated sodium chloride solution
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customto give a yellow oil
8. stirringAfter stirring for 16 hours at room temperature the mixture
9. concentrationwas concentrated
10. washwashed with 10% hydrochloric acid, saturated sodium bicarbonate, water, saturated sodium chloride solution
11. dry with materialdried over magnesium sulfate
12. filtrationfiltered
13. concentrationconcentrated
14. customto give a yellow oil
15. customFurther purification by flash chromatography (silica, 30% ethyl acetate/hexane)

ORD record

ord-284c26466b6a4e0eb639a14562d74c0d

Source dataset

uspto-grants-1992_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05134128