Hydrochloric Acid → HCID 68491667, compound

Diethyl malonate (33.7 g, 0.2 mol) was dissolved in acetonitrile (200 mL), and magnesium chloride (21.4 g, 0.22 mol) was slowly added thereto at 0 to 5° C. After 10 minutes, triethylamine (44.5 g, 0.44 mol) was added dropwise thereto at 0 to 5° C., and the mixture was allowed to react for 1 hour at room temperature. To the reaction mixture, 4-ethoxy-1,1,1-trifluoro-3-butene-2-one (37.0 g, 0.22 mol) was added dropwise at 0 to 5° C., and the mixture was allowed to react for 1 hour at room temperature. The reaction mixture was poured into diluted hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water, dried, and concentrated. Thus obtained oily product was dissolved in toluene (100 mL), p-toluenesulfonic acid (5 g) was added thereto, and the mixture was allowed to react for 3 hours under heating. After cooling, the solvent was distilled off, and thus obtained crystal was recrystallized from ethyl acetate, to obtain 31.8 g of a desired product (yield: 67%).

1. customat 0 to 5° C
2. customat 0 to 5° C.
3. customto react for 1 hour at room temperature
4. customto react for 1 hour at room temperature
5. extractionextracted with ethyl acetate
6. washThe organic layer was washed with water
7. customdried
8. concentrationconcentrated
9. dissolutionThus obtained oily product was dissolved in toluene (100 mL)
10. additionp-toluenesulfonic acid (5 g) was added
11. customto react for 3 hours
12. temperatureunder heating
13. temperatureAfter cooling
14. distillationthe solvent was distilled off
15. customthus obtained crystal was recrystallized from ethyl acetate

ORD record

ord-8a1a2f2acec948b08fd7ff72056f33f1

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08076487B2