반응 #347267

반응 방정식

potassium tert.-butoxide

2-hydroxy-acetophenone

HCl

potassium tert.-butoxide

3-methoxy-2-nitrobenzoyl chloride

→

1-(2-hydroxyphenyl)-3-(3-methoxy-2-nitrophenyl)propane-1,3-dione

수율 94.1%

용매

THF

THF

CH2Cl2

THF

THF

반응 조건

후처리

1. 1
   기타the temperature below 5° C
2. 2
   온도The resulting yellow paste is warmed to 25° C.
3. 3
   온도The mixture is cooled to 0° C.
4. 4
   기타the temperature below 5° C
5. 5
   온도The mixture is warmed to 25° C.
6. 6
   workup.STIRRINGstirred for 1 hour
7. 7
   온도The mixture is cooled to 5° C.
8. 8
   기타forming a dark brown paste
9. 9
   온도the mixture is heated
10. 10
    온도at reflux for 3 hours
11. 11
    온도The mixture is cooled to 25° C.
12. 12
    농축The mixture is concentrated under reduced pressure
13. 13
    기타to leave a brown solid
14. 14
    세척H2O (50 mL), washed with saturated NaHCO3 solution (200 mL), saturated brine (200 mL), and H2O (200 mL)
15. 15
    건조The organic layer is dried (Na2SO4)
16. 16
    농축concentrated under reduced pressure

실험 절차

To a 300-mL, three-neck, round-bottom flask with a mechanical stirrer is added potassium tert.-butoxide (2.5 g, 22 mmol). The flask is cooled to 0° C. and dry THF (10 mL) is added. To this solution, 2-hydroxy-acetophenone (3.5 mL, 18.6 mmol) in THF (10 mL) is added slowly over 30 minutes keeping the temperature below 5° C. The resulting yellow paste is warmed to 25° C. and stirred for 35 minutes. The mixture is cooled to 0° C. and 3-methoxy-2-nitrobenzoyl chloride (4.3 g, 20 mmol) in THF (15 mL) is added slowly over 15 minutes, keeping the temperature below 5° C. The mixture is warmed to 25° C. and stirred for 1 hour. The mixture is cooled to 5° C. and solid potassium tert.-butoxide (2.5 g, 22 mmol) is added forming a dark brown paste. THF (30 mL) is added and the mixture is heated at reflux for 3 hours. The mixture is cooled to 25° C. and 3N HCl is added until the pH falls to 2. The mixture is concentrated under reduced pressure to leave a brown solid. The brown solid is dissolved in CH2Cl2 (200 mL) and H2O (50 mL), washed with saturated NaHCO3 solution (200 mL), saturated brine (200 mL), and H2O (200 mL). The organic layer is dried (Na2SO4) and concentrated under reduced pressure to yield 1-(2-hydroxyphenyl)-3-(3-methoxy-2-nitrophenyl)propane-1,3-dione (5.52 g, 79%) as a tautomeric mixture.

출처