Water → 2-(5-Ethylpyridin-2-yl)ethyl methanesulfonate

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Reaction Steps

In 800 ml of methylene chloride was dissolved 80 g of (5-ethyl-2-pyridyl)ethanol, to which was added 55 g of triethylamine. To this mixture was added dropwise gradually 73.2 g of methanesulfonyl chloride while stirring under cooling, and the mixture was stirred for 3 hours at room temperature. To the reaction mixture was added 400 ml of water. The aqueous layer was separated and subjected to re-extraction, which was combined with the extracted organic layer. The resultant organic layer was washed with 400 ml of a saturated aqueous solution of sodium hydrogencarbonate, then with a saturated aqueous saline solution, followed by drying over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give 121 g (100 %) of (5-ethyl-2-pyridyl)ethyl methanesulfonate as a pale yellow oily product.

Provenance & Evidence