反应详情

温度

-20 °C

5-Methoxy-2-nitro-benzaldehyde (5.00 g, 0.0276 mol), Platinum dioxide (400 mg, 0.002 mol) and Sodium acetate trihydrate (300 mg, 0.002 mol) were placed in a pressure flask, followed by Ethyl acetate (200 mL, 2 mol). The reaction mixture was then purged under N2 at least 3 times, and H2 was introduced (purged 3 times) and maintained at 52 psi for 3 hours. The reaction mixture was then filtered, and cooled to at −20° C. N,N-Diisopropylethylamine (7.21 mL, 0.0414 mol) was added to the solution followed by Acetyl chloride (2.36 mL, 0.0331 mol). The reaction mixture was allowed to stir for 2 hours, and quenched with KHCO3 (sat). Organic layer was separated, and washed with waster, brine and dried over Na2SO4. Removal of solvent gave a crude product, which was then purified via chromatography (SiO2, 80 g, 0-100% ethyl acetate/hexanes; 4.28 g, 80%). 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 2.25 (s, 3H) 3.88 (s, 3H) 7.10-7.26 (m, 2H) 8.69 (d, J=9.06 Hz, 1H) 9.90 (s, 1H) 10.75-11.04 (m, 1H). MS (ESI, M+1): 194.10.

1. customThe reaction mixture was then purged under N2 at least 3 times, and H2
2. additionwas introduced
3. custom(purged 3 times)
4. temperaturemaintained at 52 psi for 3 hours
5. filtrationThe reaction mixture was then filtered
6. customquenched with KHCO3 (sat)
7. customOrganic layer was separated
8. washwashed with waster, brine
9. dry with materialdried over Na2SO4
10. customRemoval of solvent