反应详情

温度

0 °C

A solution of 3-(4-benzyloxy-2-formyl-phenyl)-acrylic acid tert-butyl ester (6.70 g, 19.8 mmol) in tert-butanol (150 mL) was treated with 2-methyl-2-butene (50 mL) and cooled to 0° C. A solution of NaClO2 (17.0 g, 188 mmol) and NaH2PO4 (17.0 g, 142 mmol) in H2O (200 mL) was added, and the mixture was stirred at 0° C. for 15 min. The ice bath was removed, and the mixture was stirred at room temperature for 2 h. The organic layer was separated, and the aqueous layer was extracted with EtOAc (2×100 mL). The combined organic layers were dried (Na2SO4) and concentrated. The residue was purified using silica gel chromatography (hexanes/EtOAc 9/1 to 0/10) to afford the title compound as white solid (6.78 g, 96%). 1H NMR (400 MHz, CDCl3): δ 1.52 (s, 9H), 5.12 (s, 2H), 6.20 (d, 1H, J=16.2 Hz), 7.13 (dd, 1H, J=3.6, 9.0 Hz), 7.34-7.45 (m, 5H), 7.58 (d, 1H, J=8.8 Hz), 7.64 (d, 1H, J=2.4 Hz), 8.41 (d, 1H, J=16.2 Hz).

1. customThe ice bath was removed
2. stirringthe mixture was stirred at room temperature for 2 h
3. customThe organic layer was separated
4. extractionthe aqueous layer was extracted with EtOAc (2×100 mL)
5. dry with materialThe combined organic layers were dried (Na2SO4)
6. concentrationconcentrated
7. customThe residue was purified