Pyridine → HCID 19359917, compound

Participants

Reaction Steps

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).

Provenance & Evidence