Isatin → 1-Allylisatin

Isatin (10.102 g, 68.7 mmol) was dissolved in 100 mL dry DMF, and Cs2CO3 (24.609 g, 75.5 mmol) was added. To the resulting purple-brown suspension was added allyl bromide (7.2 mL, 83 mmol) and the reaction was stirred at room temperature for 16 h. The resulting cloudy orange-brown mixture was concentrated in vacuo, and the residue was partitioned between EtOAc (160 mL) and water (80 mL). The layers were separated, and the aqueous layer was extracted with additional EtOAc (2×80 mL). The combined organic phases were dried over Na2SO4, filtered, and concentrated in vacuo. To the residue was added 300 mL hexanes. The mixture was heated to 70° C. with a water bath, and EtOAc was added until the compound went into solution (approx. 80 mL EtOAc). A small amount of insoluble red material was removed, and then the solution was allowed to cool. The resulting red crystals were filtered, washed with 3×30 mL hexanes, and then dried under vacuum to provide the title compound (11.740 g, 91%). 1H NMR (600 MHz, CHLOROFORM-D) δ ppm 4.36 (d, J=5.6 Hz, 2H), 5.26-5.34 (m, 2H), 5.78-5.88 (m, 1H), 6.88 (d, J=7.9 Hz, 1H), 7.11 (t, J=7.6 Hz, 1H), 7.56 (td, J=7.8, 1.3 Hz, 1H), 7.61 (d, J=7.4 Hz, 1H). MS (ESI) (M+H)+=188.

1. concentrationThe resulting cloudy orange-brown mixture was concentrated in vacuo
2. customthe residue was partitioned between EtOAc (160 mL) and water (80 mL)
3. customThe layers were separated
4. extractionthe aqueous layer was extracted with additional EtOAc (2×80 mL)
5. dry with materialThe combined organic phases were dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. additionTo the residue was added 300 mL hexanes
9. temperatureThe mixture was heated to 70° C. with a water bath
10. additionEtOAc was added until the compound
11. customA small amount of insoluble red material was removed
12. temperatureto cool
13. filtrationThe resulting red crystals were filtered
14. washwashed with 3×30 mL hexanes
15. customdried under vacuum

ORD 기록

ord-b932260e7be546a496e2188e3c00e3da

출처 데이터셋

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07868181B2