反应详情

To a stirred solution of 2,3-dimethoxybenzonitrile (25)(5.0 g, 30 mmol) in Et2O (12.5 mL) under N2 atmosphere was added methylmagnesium bromide (37% in Et2O) (12.5 mL, 37 mmol). The mixture was stirred for 16 h, and then 50% AcOH (20 mL) was added. After it was stirred for 30 min, the solution was poured into crushed ice, extracted with CH2Cl2, washed with 10% Na2CO3 and then with water, dried over MgSO4 and concentrated. The crude was purified by column chromatography (SiO2, n-hexane: EtOAc=4:1) to give 26. Liquid; yield: 92.5%; 1H-NMR (CDCl3, 200 MHz): δ 2.56 (s, 3H), 3.82 (s, 3H), 3.85 (s, 3H), 6.99-7.02 (m, 2H), 7.13-7.18 (m, 1H); 13C-NMR (CDCl3, 50 MHz): δ 31.18, 55.98, 61.29, 115.83, 120.80, 123.94, 133.62, 148.63, 153.04, 200.26; Anal. calcd for C10H12O3: C, 66.65; H, 6.71. Found: C, 66.60; H, 6.73.

1. stirringAfter it was stirred for 30 min
2. additionthe solution was poured
3. custominto crushed ice
4. extractionextracted with CH2Cl2
5. washwashed with 10% Na2CO3
6. dry with materialwith water, dried over MgSO4
7. concentrationconcentrated
8. customThe crude was purified by column chromatography (SiO2, n-hexane: EtOAc=4:1)