반응 #537264

반응 방정식

2-methoxy-5-nitro benzoyl chloride

magnesium chloride

diethyl malonate

triethylamine

hydrochloric acid

→

1-(2-Methoxy-5-nitro-phenyl)-ethanone

수율 78.0%

용매

ethyl acetate

DMSO water

toluene

반응 조건

후처리

1. 1
   기타to attain room temperature
2. 2
   workup.STIRRINGthen stirred for 30 min
3. 3
   기타The organic layer was separated
4. 4
   세척washed with water
5. 5
   기타dried
6. 6
   농축Concentration under reduced pressure
7. 7
   기타gave a residue to which
8. 8
   온도The mixture was heated to 140° C. for 2 hr
9. 9
   온도cooled to RT
10. 10
    세척The organic layer was washed successively with water, bicarbonate solution, and brine
11. 11
    기타dried
12. 12
    기타Evaporation under reduced pressure

실험 절차

Anhydrous magnesium chloride (150 mg, 1.6 mmol) was added to a solution of diethyl malonate (440 mg, 2.76 mmol) and triethylamine (670 mg, 6.5 mmol) in dry toluene (10 ml) at room temperature under inert atmosphere. After stirring for 1 hr, the reaction was cooled to 0° C. and 2-methoxy-5-nitro benzoyl chloride (550 mg, 2.3 mmol) was added. The reaction mixture was allowed to attain room temperature then stirred for 30 min before adding 6N hydrochloric acid (15 ml). The organic layer was separated, washed with water and dried. Concentration under reduced pressure gave a residue to which was added 1:1 DMSO-water (10 ml). The mixture was heated to 140° C. for 2 hr, then cooled to RT and diluted with ethyl acetate (50 ml). The organic layer was washed successively with water, bicarbonate solution, and brine, then dried. Evaporation under reduced pressure gave 1-(2-Methoxy-5-nitro-phenyl)-ethanone (350 mg, 70%) as a solid.

출처