反应详情

MeOH (28 mL) was added to a flask containing 4-(1-benzylamino-ethylidene)-pent-2-enedioic acid dimethyl ester (1.0 g, 3.46 mmol). NaOMe solution (7 mL, 3.46 mmol, 0.5M in MeOH) and N-bromosuccinimide (0.74 g, 4.15 mmol) were added. The resulting mixture was refluxed for 1 h. After cooling to r.t., the solvent was evaporated in vacuo. The residue was partitioned between saturated NH4Cl (50 mL) and CH2Cl2 (50 mL). The aqueous layer was extracted with additional CH2Cl2 and the organic layers were combined, dried over MgSO4, and concentrated. The crude product was chromatographed (0-40% EtOAc/hexanes) to give 0.77 g of the title compound. MS: (+) m/z 357.95, 359.92 (M+Na, 79/81Br).

1. temperatureThe resulting mixture was refluxed for 1 h
2. customthe solvent was evaporated in vacuo
3. customThe residue was partitioned between saturated NH4Cl (50 mL) and CH2Cl2 (50 mL)
4. extractionThe aqueous layer was extracted with additional CH2Cl2
5. dry with materialdried over MgSO4
6. concentrationconcentrated
7. customThe crude product was chromatographed (0-40% EtOAc/hexanes)