4-Toluenesulfonyl chloride → HCID 21107319, compound

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Reaction Steps

A solution of 2,3-dihydro-1H-pyrano[3,2-f]quinolin-2-ol (intermediate 10) (0.47 g, 2.3 mmol) and p-toluene sulfonyl chloride (0.89 g, 4.6 mmol) in anhydrous pyridine (20 mL) was stirred at room temperature for 2.5 days. It was then poured into ice-H2O and extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. Chromatography ((15:4:1) EtOAc-Hexane-MeOH) afforded 0.77 g (93%) of 2,3-dihydro-1H-pyrano[3,2-f]quinolin-2-yl 4-methylbenzenesulfonate as an off-white solid: mp 167.5–169.5° C. MS ESI m/z 356 [M+H]+. Elemental Analysis for C19H17NO4S: Calculated: C, 64.21; H, 4.82; N, 3.94. Found: C, 63.98; H, 4.79; N, 3.84.

Provenance & Evidence