Dimethyl Sulfoxide → Phthalimide, N-(2-formylethyl)-

Temperature

-78 °C

The reaction was carried out with oven dried glassware. DMSO (85 μl, 1.1 mmol) was added to oxalyl chloride solution (0.35 mL 2 M DCM solution with 5 mL dry DCM) at −78° C. The reaction mixture was stirred at −78° C. for 10 min. 2-(3-Hydroxy-propyl)-isoindole-1,3-dione solution (102 mg, 0.5 mmol, in 2 mL DCM) was added drop wise in 2 min. Then triethylamine (0.35 mL, 2.5 mmol) was added drop wise in 2 min. The mixture was stirred for additional 30 minutes at −78° C. and was warmed up to room temperature. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, dried over MgSO4, filtered, and the filtrated was concentrated in vacuo. The crude product was purified by flash chromatography to give 3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionaldehyde.

1. customThe reaction was carried out with oven
2. customdried glassware
3. stirringThe mixture was stirred for additional 30 minutes at −78° C.
4. temperaturewas warmed up to room temperature
5. extractionThe reaction mixture was extracted with ethyl acetate
6. washThe organic layer was washed with saturated sodium bicarbonate
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationthe filtrated was concentrated in vacuo
10. customThe crude product was purified by flash chromatography

ORD record

ord-2bd4809f898c4c5eb0d4cf0dab616244

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07608723B2