Phthalimide → 2-(Undec-10-en-1-yl)-1H-isoindole-1,3(2H)-dione

To a mixture of 10-undecen-1-ol (4.23 g, 24.8 mmol), phthalimide (3.65 g, 24.8 mmol) and triphenylphosphine (6.51 g, 24.8 mmol) in anhydrous tetrahydrofuran (30 ml), a solution of DEAD (3.9 ml, 24.8 mmol) in anhydrous tetrahydrofuran (10 ml) was slowly added while keeping the temperature below 8-10° C. After 2 hours further DEAD (1.0 ml, 6.37 mmol) and triphenylphosphine (1.3 g, 4.96 mmol) were added and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated and the residue was triturated with diethyl ether (50 ml). The solid was removed by filtration and washed with diethyl ether (2×50 ml). The combined filtrates were concentrated and the residue was triturated with hexane (50 ml) at 40° C. The resulting solid was removed by filtration and washed with hexane (2×50 ml). The combined filtrates were concentrated and the residue was purified by column chromatography eluting with 10:2 hexane:ethyl acetate mixture. The product was obtained as a low-melting white solid (4.9 g, 66% yield).

1. customthe temperature below 8-10° C
2. concentrationThe reaction mixture was concentrated
3. customthe residue was triturated with diethyl ether (50 ml)
4. customThe solid was removed by filtration
5. washwashed with diethyl ether (2×50 ml)
6. concentrationThe combined filtrates were concentrated
7. customthe residue was triturated with hexane (50 ml) at 40° C
8. customThe resulting solid was removed by filtration
9. washwashed with hexane (2×50 ml)
10. concentrationThe combined filtrates were concentrated
11. customthe residue was purified by column chromatography
12. washeluting with 10:2 hexane

ORD record

ord-10e97c494d8b491d801ea93face16dec

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09233115B2