Triethylamine → (2-Methoxy-6-methylbenzyl)phthalimide

To a solution of 2-methoxy-6-methylbenzyl alcohol (0.96 g, 6.32 mmol) in CH2Cl2 (35 mL) was added triethylamine (2.00 mL, 14.35 mmol) followed by methanesulfonyl chloride (0.90 mL, 11.63 mmol) and the resultant solution was heated at 40° C. for 45 minutes then cooled to room temperature. The mixture was diluted with CH2Cl2 (35 mL), washed with brine (3×15 mL), dried (Na2SO4), and concentrated to provide a pale yellow solid. The solid (1.12 g) was dissolved in DMF (35 mL), treated with potassium phthalimide (2.62 g, 14.15 mmol), and heated at 80° C. overnight. The mixture was cooled to room temperature and diluted with EtOAc (70 mL), brine (35 mL), and water (20 mL). The phases were separated and the organic phase was washed with 1.0 N NaOH (6×10 mL) and brine (2×20 mL). The organic phase was dried (MgSO4) and concentrated to provide an pale yellow solid. The solid was rinsed with hexanes (3×10 mL) and provided 1.18 g (66%) of (2-methoxy-6-methylbenzyl)phthalimide as a white solid. 1H NMR (CDCl3) δ 2.53 (s, 3H), 3.75 (s, 3H), 4.89 (s, 2H), 6.70 (d, 1H, J=8.4 Hz), 6.80 (d, 1H, J=7.5 Hz), 7.15 (dd, 1H, J=7.5, 8.4 Hz), 7.66–7.68 (m, 2H), 7.76–7.80 (m, 2H); 13C NMR (CDCl3) δ 20.27, 34.95, 55.90, 108.61, 122.38, 123.17, 123.41, 128.97, 132.60, 134.07, 139.55, 158.70, 168.36.

1. washwashed with brine (3×15 mL)
2. dry with materialdried (Na2SO4)
3. concentrationconcentrated
4. customto provide a pale yellow solid
5. temperatureheated at 80° C. overnight
6. temperatureThe mixture was cooled to room temperature
7. customThe phases were separated
8. washthe organic phase was washed with 1.0 N NaOH (6×10 mL) and brine (2×20 mL)
9. dry with materialThe organic phase was dried (MgSO4)
10. concentrationconcentrated
11. customto provide an pale yellow solid
12. washThe solid was rinsed with hexanes (3×10 mL)

ORD-Eintrag

ord-7ef5756414e1483ebd37c8a4117aa494

Quelldatensatz

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07091217B2