反应详情

To a stirred mixture of sodium hydride (110 mg, 60%, 2.75 mmol) in THF (8 mL) at room temperature, was added iodomethane (0.54 grams, 3.78 mmol) followed by 3-(3'-ethoxy-4'-methoxyphenyl)-3-phthalimido-1-propanol (850 mg, 2.39 mmol). The mixture was stirred at room temperature for 15 h. To the mixture was added NH4Cl (20 mL, sat). The organic layer was separated. The aqueous layer was extracted with methylene chloride (2×50 mL). The combined organic layers were washed with brine (50 mL) and dried over magnesium sulfate. Removal of solvent and chromatography (silica gel 200 grams, 1:12 EtOAc:CH2Cl2) gave 3-(3'-ethoxy-4'-methoxyphenyl)-1-methoxy-3-phthalimidopropane as an oil (360 mg, 41% yield). The resulting oil solidified after standing at room temperature over weekend: mp, 67.5°-70.0° C.; 1H NMR (CDCl3)δ1.45 (t, J=7 Hz, 3H, CH3), 2.50-2.60 (m, 1H, CHH), 2.71-2.85 (m, 1H, CHH), 3.26 (s, 3H, CH3), 3.39 (t, J=6 Hz, 2H, CH2), 3.84 (s, 3H, CH3), 4.10 (q, J=7 Hz, 2H, CH2), 5.47 (dd, J=7, 9.3 Hz, 1H, NCH), 6.81 (d, J=Hz, 1H, Ar), 7.09-7.16 (m, 2H, Ar), 7.66-7.69 (m, 2H, Ar), 7.76-7.82 (m, 2H, Ar). 13C NMR (CDCl3)δ(APT) 14.67 (CH3), 31.23 (CH2), 51.89 (CH3), 58.63 (CH), 64.25 (CH2), 69.62 (CH2), 111.13 (CH), 112.98 (CH), 120.58 (CH), 123.06 (CH), 131.87 (C), 131.92 (C), 133.78 (CH), 148.09 (C), 148.84 (C), 168.33 (C); Anal Calcd for C21H23NO5 0.05H2O: C, 67.66; H, 6.23; N, 3.75. Found: C, 67.91; H, 6.00; N, 3.71.

1. customThe organic layer was separated
2. extractionThe aqueous layer was extracted with methylene chloride (2×50 mL)
3. washThe combined organic layers were washed with brine (50 mL)
4. dry with materialdried over magnesium sulfate
5. customRemoval of solvent and chromatography (silica gel 200 grams, 1:12 EtOAc:CH2Cl2)