Water → 2-(4-chlorobut-2-yn-1-yl)-2,3-dihydro-1H-isoindole-1,3-dione

HRID 1620544Notes

Reaction equation

[C:1]1(=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:10])[NH:2]1.C(=O)([O-])[O-].[K+].[K+].[Cl:18][CH2:19][C:20]#[C:21][CH2:22]Cl.O>CN(C=O)C>[Cl:18][CH2:19][C:20]#[C:21][CH2:22][N:2]1[C:3](=[O:10])[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:1]1=[O:11]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1H-isoindole-1,3(2H)-dione (441 mg) in DMF (5 mL) were added potassium carbonate (829 mg) and 1,4-dichlorobut-2-yne (2.21 g) at room temperature. The reaction mixture was stirred at 80° C. for 5 hr. The reaction mixture was added to water at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (202 mg).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record: ord-943fa8593c7e4b0db2688633f1f375b3
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772277B2

Reaction notes

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