Molbank 2006, M459 |
2-(1-ethyl-but-2-enyloxy)-isoindole-1,3-dione
Received:
A
degassed mixture containing 0.416 mmol 3-hexene and 0.083 mmol
N-hydroxyphthalimide (NHPI),1,2 in 5 mL acetonitrile was added to a degassed solution of lead
tetraacetate3 (0.041mmol in 5 mL acetonitrile) under nitrogen atmosphere at room
temperature. After the completion of the reaction, the solvent and the olefin
excess was removed under reduced pressure and the residue was purified by
preparative TLC using hexane:ethyl
acetate = 2:1 as eluent, giving the above product.
1H-NMR (400 MHz, CDCl3): d= 7.82, 7.76 (Ar, 4 H); 5.65, 5.59 (CH=CH, 2H); 4.83 (O-CH, 1H); 1.51 (CH2, 2H); 1.03, 0.84 (CH3, 6H).
13C-NMR (100 MHz, CDCl3): d= 164.6 (C=O); 134.9, 130.6 (Ar); 84.2 (C-O); 77.5 (C=C); 32.8 (CH2); 24.2, 38.6 (CH3).
References:
1. Ishii, Y.; Sakaguchi, S.; Iwahama, T., Adv. Synth. Catal., 2001, 343, 393.
2. Masui, M.; Hosomi, K.; Tsuchida, K.; Ozaki, S., Chem. Pharm. Bull., 1985, 33, 4798.
3. Martin, J.C.;
Sample Availability: Available from MDPI.
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