Ethyl Acetate → HCID 70237236, compound

Participants

Reaction Steps

A solution of 80 (53 mg, 112 μmol) in benzene (5 mL) was added to a mixture of 50% aqueous NaOH (0.5 g) and benzyltributylammonium chloride (70 mg, 224 μmol, 2 equiv). The mixture was stirred vigorously for 15 min and 100 (147 mg, 556 μmol, 5 equiv) was added. The mixture was stirred vigorously for 12 h at 25° C. Ice-cold H2O (50 mL), and EtOAc (10 mL) were added. The aqueous layer was extracted with EtOAc (10 mL), the combined organic layers were dried (Na2SO4) and the solvent was removed under vacuum. Chromatography (SiO2, 2×20 cm, 10-25% EtOAc-hexane gradient elution) afforded 108 (58 mg, 72 mg theoretical, 80%) as an oil: 1H NMR (CDCl3, 400 MHz) δ 8.31 and 8.27 (two d, J=8.3, 8.8 Hz, 1H), 8.21 (d, J=8.2 Hz, 1H), 7.61-7.49 (m, 4H), 7.42-7.33 (m, 3H), 6.82-6.69 (m, 1H), 6.21 (m, 0.5H), 6.13 (d, 0.5H), 5.32-5.17 (m, 2H), 5.01 (dt, J=12.2, 7.5 Hz, 0.5H), 4.86 and 4.82 (two m, 1H), 4.41 (m, 0.5H), 3.81 (m, 2H), 3.51 (m, 1H), 3.36-3.21 (m, 1H), 2.12 and 1.92 (two m, 2H), 1.83-1.49 (m, 8H), 1.29 (s, 9H); IR (film) νmax 2940, 1699, 1591, 1407, 1366, 1338, 1158, 1099, 1037 cm−1.

Provenance & Evidence