4-Toluenesulfonyl chloride → 1H-Isoindole-1,3(2H)-dione, 2-[3-[[(4-methylphenyl)sulfonyl]oxy]propyl]-

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(3-hydroxypropyl) isoindoline-1,3-dione (1.8 g, 8.77 mmol) in CH2Cl2 (30 mL, 3 mL/mmol) was added Et3N (2 mL, 13.1 mmol). After stirring for 10 min at 0° C., tosylchloride (2 g, 10.5 mmol) was added and the reaction was stirred for 12 h at RT. The reaction was quenched with water and extracted with CH2Cl2 (2×50 mL). The organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography provided 3-(1,3-dioxoisoindolin-2-yl)propyl 4-methylbenzenesulfonate (3 mg, 96%). Observed mass (M+1): 360.1.

Provenance & Evidence