Water → 2-[(2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methyl]-1H-isoindole-1,3(2H)-dione

HRID 1850412Notes

Reaction equation

[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].CN(C=O)C.I[CH2:19][C:20]1([CH3:32])[CH2:24][C:23]2[C:25]([CH3:31])=[CH:26][C:27]([CH3:30])=[C:28]([CH3:29])[C:22]=2[O:21]1.O>C(OCC)(=O)C>[CH3:19][C:20]1([CH2:32][N:5]2[C:1](=[O:11])[C:2]3[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4]2=[O:6])[CH2:24][C:23]2[C:25]([CH3:31])=[CH:26][C:27]([CH3:30])=[C:28]([CH3:29])[C:22]=2[O:21]1

Participants

Conditions

Temperature: 140 °C

Procedure

Potassium phthalimide (702 mg, 3.79 mmol) was added to a solution of DMF (10 mL) containing 2-(iodomethyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran (1.00 g, 3.16 mmol) synthesized in Reference Example 126, and the mixture was stirred at 140° C. for 15 hours. After that, the reaction solution was cooled to room temperature, and water and ethyl acetate were added thereto to separate an organic layer. The organic layer was washed with water and saturated saline, and dried using anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was purified by silica gel chromatography (hexane-ethyl acetate 95:5-75:25) to give 730 mg of the title compound (yield: 69%)

Workup

customsynthesized in Reference Example 126
temperatureAfter that, the reaction solution was cooled to room temperature
customto separate an organic layer
washThe organic layer was washed with water and saturated saline
customdried
concentrationfollowed by concentration under reduced pressure
customThe residue was purified by silica gel chromatography (hexane-ethyl acetate 95:5-75:25)

Sources & evidence

ORD record: ord-aec158f8674a426db0a32a2f6a8ab0ac
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957069B2

Reaction notes

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