Hydrochloric Acid → HCID 19363275, compound

N-2-(4-Hydroxyphenyl)ethyl-3-pentyloxyphthalimide (412 mg, 1.17 mmol) was dissolved in THF (1 ml), and a 1.0M THF solution (4 ml) of BH3·THF (4.0 mmol) was added to this solution. The mixture was stirred with refluxing under heating for 8 hours. A 3N aqueous hydrochloric acid solution (10 ml) was added to the reaction mixture. The mixture was further stirred for 0.5 hour at the same temperature, and water (20 ml) was added. The mixture was extracted with ethyl acetate (20 ml×3), and washed with a saturated aqueous sodium hydrogencarbonate solution (20 ml) and saturated brine (30 ml). The organic layer was dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1) to give N-2-(4-hydroxyphenyl)ethyl-7-pentyloxyisoindol-1-one (232 mg, 0.68 mmol, 59%) as colorless crystals.

1. temperaturewith refluxing
2. temperatureunder heating for 8 hours
3. additionwas added
4. extractionThe mixture was extracted with ethyl acetate (20 ml×3)
5. washwashed with a saturated aqueous sodium hydrogencarbonate solution (20 ml) and saturated brine (30 ml)
6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
7. filtrationThe drying agent was filtered off
8. concentrationthe filtrate was concentrated under reduced pressure
9. customThe obtained residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1)

ORD record

ord-bd35a24d7b8d4297900f144bb88df26a

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06017919