3-Chlorobenzaldehyde → cis-N-[4-(3-chlorophenyl)-but-3-enyl]-phthalimide

Temperatur

-75 °C

To a stirred suspension of (3-(1,3-dioxoisoindolin-2-yl)propyl)triphenylphosphonium bromide (17.6 g, 33.2 mmol) in tetrahydrofuran (170 mL) at ambient temperature was added 3-chlorobenzaldehyde (3.76 mL, 33.2 mmol), and the resulting mixture was cooled with a dry-ice acetone bath to −75° C. Solid potassium t-butoxide (3.72 g, 33.2 mmol) was added, and stirring was continued in the bath for an additional 20 minutes; the temperature was −80° C. The cooling bath was removed, and when the internal temperature reached −30° C., the flask was placed in a water-ice bath. The temperature eventually settled at 10° C. and was maintained for 2 hours. The reaction mixture was poured into a separatory funnel containing water (250 mL), and this was extracted with ethyl acetate (250 mL). The organic layer was dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel, eluting with 90/10 hexanes/ethyl acetate, to afford (Z)-2-(4-(3-chlorophenyl)but-3-enyl)isoindoline-1,3-dione as a white solid (8.46 g, 82% yield).

1. customwas −80° C
2. customThe cooling bath was removed
3. customreached −30° C.
4. customthe flask was placed in a water-ice bath
5. customeventually settled at 10° C.
6. temperaturewas maintained for 2 hours
7. additionThe reaction mixture was poured into a separatory funnel
8. additioncontaining water (250 mL)
9. extractionthis was extracted with ethyl acetate (250 mL)
10. dry with materialThe organic layer was dried over sodium sulfate
11. concentrationconcentrated
12. customThe residue was purified by chromatography on silica gel
13. washeluting with 90/10 hexanes/ethyl acetate

ORD-Eintrag

ord-d88aa51af29e45db999f2ad28496616a

Quelldatensatz

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09096567B2