Reacción #417965

Ecuación de reacción

Acetic anhydride

5-amino-2-methyl phenol

3-bromophenetole

Cs2CO3

→

product 18a

N-[4-methyl-3-(2-phenoxy-ethoxy)-phenyl]-acetamide

Disolventes

acetic acid

water

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction was refluxed for 5 mins
2. 2
   FiltraciónIt was filtered off
3. 3
   Lavadowashed with water (4 mL)
4. 4
   Otrodried
5. 5
   Otroto obtain the product along with the trace amount of O-acylated product
6. 6
   Extracciónextracted with ethyl acetate (3×20 mL)
7. 7
   SecadoThe combined extracts were dried over sodium sulfate
8. 8
   Otrorecrystallized from toluene

Procedimiento

Acetic anhydride (1.25 mL, 12.2 mmol) was added to a solution of 5-amino-2-methyl phenol (1.0 g, 8.1 mmol) in acetic acid (6 mL), and the reaction was refluxed for 5 mins. Then the reaction mixture was cooled to room temperature and the product was solidified. It was filtered off and washed with water (4 mL) and dried to obtain the product along with the trace amount of O-acylated product. The mixture, to which was added 3-bromophenetole (1.33 g, 6.6 mmol) and Cs2CO3 (2.927 g, 9.0 mmol) in DMF (10 mL), was stirred overnight at 50° C. The reaction mixture was then diluted with water (10 mL) and extracted with ethyl acetate (3×20 mL). The combined extracts were dried over sodium sulfate and recrystallized from toluene to obtain the pure product 18a in 65% (yield over two steps) as an off-white solid.

Fuente