2-Bromothiophene → HCID 19885898、化合物

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) gave 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
9. concentrationthe mixture was 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レコード

ord-e6c75a5b3456483383d4cfa372eef8e9

出典データセット

uspto-grants-1992_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05134128