反应详情

997 mg of tricyclohexyl [o-(1-hydroxyethyl)phenyl]tin (2.04 mmol) and 20 ml of pyridine were mixed together in a 20 ml two-neck flask, then 269 mg of methane sulfonyl chloride (2.35 mmol) was added dropwise thereto. After the mixture was stirred for 22 hours at a room temperature, a brown-colored solid, which had been obtained by concentrating the reaction solution under reduced pressure, was dissolved in 10 ml of dimethylformamide. Subsequently, 10 ml of a dimethylformamide solution containing 354 mg of sodium azide (5.44 mmol) was added dropwise, and the mixture was then refluxed for 3 hours. After the mixture was cooled to 0° C., and 20 ml of water was added, the organic substance was extracted with 30 ml of ether three times. After the ether layer was washed with 30 ml of a saturated brine, and dried over sodium sulfate, the solvent was removed under reduced pressure to yield a crude product. The resultant crude product was purified by column chromatography on silica gel (for which, 50 g of silica gel, and hexane, as a devleoping solvent were employed) to yield 288 mg of the final product (0.559 mmol).

1. customa brown-colored solid, which had been obtained
2. concentrationby concentrating the reaction solution under reduced pressure
3. dissolutionwas dissolved in 10 ml of dimethylformamide
4. additionwas added dropwise
5. temperaturethe mixture was then refluxed for 3 hours
6. temperatureAfter the mixture was cooled to 0° C.
7. extractionthe organic substance was extracted with 30 ml of ether three times
8. washAfter the ether layer was washed with 30 ml of a saturated brine
9. dry with materialdried over sodium sulfate
10. customthe solvent was removed under reduced pressure
11. customto yield a crude product
12. customThe resultant crude product was purified by column chromatography on silica gel (for which, 50 g of silica gel, and hexane