Hydrochloric Acid → (1R*,5S*)-3-(4-bromo-2,6-diethylphenyl)-1-methyl-8-oxabicyclo[3.2.1]octane-2,4-dione

温度

80 °C

(1R*,5S*)-1-Methyl-8-oxabicyclo[3.2.1]octane-2,4-dione (1 g, 6.5 mmol) and 4-dimethylamino-pyridine (3.96 g, 32.5 mmol) are added to a mixture of chloroform (20 ml) and toluene (5 ml). The reaction mixture is flushed with nitrogen for 15 minutes at ambient temperature. 4-Bromo-2,6-diethylphenyllead triacetate (4.25 g, 7.14 mmol) is added in one portion and the reaction mixture is stirred and heated to 80° C. (pre-heated oil bath) under an atmosphere of nitrogen for 1 hour. The reaction mixture is cooled to room temperature, acidified to pH 1 with 2N aqueous hydrochloric acid, filtered through a plug of diatomaceous earth and the two phases are separated. The aqueous phase is extracted with dichloromethane (2×25 ml), the organic phases are combined, washed with water, and dried over anhydrous sodium sulfate. The mixture is filtered, and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give (1R*,5S*)-3-(4-bromo-2,6-diethylphenyl)-1-methyl-8-oxabicyclo[3.2.1]octane-2,4-dione as a white solid (0.1 g).

1. customThe reaction mixture is flushed with nitrogen for 15 minutes at ambient temperature
2. temperature(pre-heated oil bath) under an atmosphere of nitrogen for 1 hour
3. temperatureThe reaction mixture is cooled to room temperature
4. filtrationfiltered through a plug of diatomaceous earth
5. customthe two phases are separated
6. extractionThe aqueous phase is extracted with dichloromethane (2×25 ml)
7. washwashed with water
8. dry with materialdried over anhydrous sodium sulfate
9. filtrationThe mixture is filtered
10. customthe filtrate is evaporated under reduced pressure
11. customThe residue is purified by column chromatography on silica gel

ORDレコード

ord-5305f318b4664de785b758d25f915c68

出典データセット

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08895761B2