Dimethylformamide → 2-(3-(2-Phenyl-1,3-dioxolan-2-yl)propyl)isoindoline-1,3-dione

HRID 1013120Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][C:5]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:9][CH2:8][CH2:7][O:6]1.[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.[K].CN(C=O)C>O>[C:10]1([C:5]2([CH2:4][CH2:3][CH2:2][N:20]3[C:16](=[O:26])[C:17]4[C:18](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:19]3=[O:21])[O:9][CH2:8][CH2:7][O:6]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Add 2-(3-chloropropyl)-2-phenyl-[1,3]dioxolane (38 g, 168 mmol) and potassium phthalimide (34.2 g, 184.4 mmol) to DMF (80 mL) and stir for 40 min at 150° C. Cool the reaction to RT, dilute with water (1 L) and extract the mixture with a mixture of EtOAc (500 mL) and hexanes (500 mL) and DCM (2 L). Dry (sodium sulfate), concentrate and recrystallize the solid from hot ethanol (600 mL). Filter and dry the residue under vacuum to isolate the title compound as a white solid (47.62 g, 84%).

Workup

temperatureCool
customthe reaction to RT
extractionextract the mixture
additionwith a mixture of EtOAc (500 mL) and hexanes (500 mL) and DCM (2 L)
dry with materialDry (sodium sulfate)
concentrationconcentrate
customrecrystallize the solid from hot ethanol (600 mL)
filtrationFilter
customdry the residue under vacuum

Sources & evidence

ORD record: ord-6e014771ee0a4e1b874404a23cd87f81
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981882B2

Reaction notes

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