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

HRID 522924Notes

Reaction equation

[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15].CCN(CC)CC.[S:23](Cl)([C:26]1[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=1)(=[O:25])=[O:24]>C(Cl)Cl>[CH3:30][C:29]1[CH:31]=[CH:32][C:26]([S:23]([O:1][CH2:2][CH2:3][CH2:4][N:5]2[C:13](=[O:14])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]2=[O:15])(=[O:25])=[O:24])=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

stirringthe reaction was stirred for 12 h at RT
customThe reaction was quenched with water
extractionextracted with CH2Cl2 (2×50 mL)
washThe organic extracts were washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customPurification by silica gel column chromatography

Sources & evidence

ORD record: ord-a22bd1da16664bf797e2d615ef5fe750
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334269B2

Reaction notes

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