反応 #417965

反応方程式

Acetic anhydride

5-amino-2-methyl phenol

3-bromophenetole

Cs2CO3

→

product 18a

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

溶媒

acetic acid

water

DMF

反応条件

後処理

1. 1
   温度the reaction was refluxed for 5 mins
2. 2
   ろ過It was filtered off
3. 3
   洗浄washed with water (4 mL)
4. 4
   その他dried
5. 5
   その他to obtain the product along with the trace amount of O-acylated product
6. 6
   抽出extracted with ethyl acetate (3×20 mL)
7. 7
   乾燥The combined extracts were dried over sodium sulfate
8. 8
   その他recrystallized from toluene

実験手順

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.

出典