反应详情

0.34 g (8.5 mmol) of a 60% oily sodium hydride was suspended in tetrahydrofuran (20 ml). A solution of 2.0 g (7.1 mmol) of 4,4-dimethyl-2-(4'-hydroxymethylbiphenyl-2-yl)oxazoline in tetrahydrofuran (30 ml) was dropwise added thereto at room temperature, followed by further stirring at room temperature for one hour. After the reaction liquid was cooled with ice, a solution of 1.6 g (8.4 mmol) of p-toluene-sulfonyl chloride in tetrahydrofuran (20 ml) was dropwise added thereto. After stirring for 3 hours as such, the reaction liquid was poured into a saturated aqueous solution of ammonium chloride, followed by the extraction with chloroform. After washing with water and drying, vacuum concentration was conducted. The residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system) to give 1.7 g of the title compound as an oil (yield 55%).

1. customat room temperature
2. customAfter the reaction liquid
3. temperaturewas cooled with ice
4. stirringAfter stirring for 3 hours as such,
5. customthe reaction liquid
6. extractionfollowed by the extraction with chloroform
7. washAfter washing with water
8. customdrying
9. concentrationvacuum concentration
10. customThe residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system)