Reacción #9000

Ecuación de reacción

methanesulfonyl chloride

potassium phthalimide

2-methoxy-6-methylbenzyl alcohol

triethylamine

→

(2-methoxy-6-methylbenzyl)phthalimide

Rendimiento 66.4%

Disolventes

EtOAc

brine

water

DMF

CH2Cl2

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with brine (3×15 mL)
2. 2
   Secadodried (Na2SO4)
3. 3
   Concentraciónconcentrated
4. 4
   Otroto provide a pale yellow solid
5. 5
   Temperaturaheated at 80° C. overnight
6. 6
   TemperaturaThe mixture was cooled to room temperature
7. 7
   OtroThe phases were separated
8. 8
   Lavadothe organic phase was washed with 1.0 N NaOH (6×10 mL) and brine (2×20 mL)
9. 9
   SecadoThe organic phase was dried (MgSO4)
10. 10
    Concentraciónconcentrated
11. 11
    Otroto provide an pale yellow solid
12. 12
    LavadoThe solid was rinsed with hexanes (3×10 mL)

Procedimiento

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.

Fuente