3,4-dihydro-2H-pyran → HCID 19841414, compound

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A solution of N,N-di(2-hydroxyethyl)-4-chloro-3-nitrobenzenesulfonamide (7.1 g, 21.9 mmol), 3,4-dihydro-2H-pyran (4.4 mL, 48 mmol) and p-toluenesulfonic acid hydrate (0.10 g) in methylene chloride (200 mL) was stirred at 20°-25° for 3 days. After washing with a saturated solution of sodium bicarbonate the organic layer was dried (Na2SO4), filtered and concentrated. Flash chromatography of the residue over silica gel with chloroform gave 9.0 g of product.

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