반응 #217894

반응 방정식

potassium carbonate

3-(4-hydroxyphenyl)-1-propanol

6-chloronicotinamide

dimethylacetamide

→

6-[4-(3-hydroxy-propyl)-phenoxy]-nicotinamide

수율 87.0%

용매

isooctane

sodium hydroxide

반응 조건

후처리

1. 1
   기타Equip the reaction setup with a Dean-Stark trap
2. 2
   온도heat
3. 3
   기타the reaction
4. 4
   온도to reflux under nitrogen for 6 h
5. 5
   온도Cool
6. 6
   기타the reaction to room temperature
7. 7
   여과filter off the solids
8. 8
   농축Concentrate on a rotary evaporator
9. 9
   기타to give the crude product
10. 10
    추출extract with ethyl acetate (4×100 mL)
11. 11
    건조dry the extracts over magnesium sulfate
12. 12
    여과filter
13. 13
    농축concentrate on a rotary evaporator
14. 14
    기타to give the crude product
15. 15
    기타The crude product is purified by flash chromatography on silica gel eluting with 1.5% concentrated ammonium hydroxide/15% ethanol/chloroform

실험 절차

Add potassium carbonate (2.2821 g, 16.51 mmol) to a stirred solution of 3-(4-hydroxyphenyl)-1-propanol (1.0041 g, 6.598 mmol), 6-chloronicotinamide (1.0038 g, 6.411 mmol), dimethylacetamide (21 mL), and isooctane (3 mL). Equip the reaction setup with a Dean-Stark trap and heat the reaction to reflux under nitrogen for 6 h. Cool the reaction to room temperature and filter off the solids. Concentrate on a rotary evaporator to give the crude product. Take the crude product up in 1 N sodium hydroxide (250 mL), extract with ethyl acetate (4×100 mL), dry the extracts over magnesium sulfate, filter, and concentrate on a rotary evaporator to give the crude product. The crude product is purified by flash chromatography on silica gel eluting with 1.5% concentrated ammonium hydroxide/15% ethanol/chloroform to yield 1.5188 g (87%) of 6-[4-(3-hydroxy-propyl)-phenoxy]-nicotinamide: mass spectrum (ion spray): m/z=273.2 (M+1); 1H NMR (DMSO-d6): 8.61 (d, 1H), 8.24 (dd, 1H), 8.03 (s, 1H), 7.48 (s, 1H), 7.25 (d, 2H), 7.07-7.03 (m, 3H), 4.50 (t, 1H), 3.46-3.41 (m, 2H), 2.63 (t, 2H), 1.77-1.70 (m, 2H).

출처