Reacción #216295

Ecuación de reacción

(1R)-1-[2-(2,4-Difluorophenyl)-2-oxiranyl]ethanol

3,5-dinitrobenzoyl chloride

→

[(1R)-1-[(2R)-2-(2,4-difluorophenyl)- 2-oxiranyl]ethyl]3,5-dinitrobenzoate

Rendimiento 46.3%

Disolventes

methylene chloride

triethylamine

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   Lavadowashed with 150 ml of water
3. 3
   Secadowith 150 ml of 5% aqueous solution of sodium bicarbonate, dried over magnesium sulfate
4. 4
   Concentraciónconcentrated under reduced pressure
5. 5
   OtroThe crystals separated out
6. 6
   Filtraciónwere collected by filtration
7. 7
   Lavadowashed with methylene chloride
8. 8
   workup.DISTILLATIONdistilled off under reduced pressure
9. 9
   workup.ADDITION25 ml of ethyl acetate and 300 ml of methanol were added to the residue
10. 10
    Temperaturathe mixture was cooled with ice
11. 11
    OtroThe crystals separated out
12. 12
    Filtraciónwere collected by filtration
13. 13
    Otrorecrystallized from a mixture of 25 ml of ethyl acetate and 250 ml of methanol

Procedimiento

(1R)-1-[2-(2,4-Difluorophenyl)-2-oxiranyl]ethanol (31.5 g) and 40 g of 3,5-dinitrobenzoyl chloride were dissolved in 500 ml of methylene chloride and, with ice cooling, 24.1 ml of triethylamine was added dropwise thereinto. The reaction solution was stirred at room temperature for 3.5 hours, washed with 150 ml of water and then with 150 ml of 5% aqueous solution of sodium bicarbonate, dried over magnesium sulfate and concentrated under reduced pressure. The crystals separated out were collected by filtration and washed with methylene chloride. The mother liquor and the washing were combined and distilled off under reduced pressure, then 25 ml of ethyl acetate and 300 ml of methanol were added to the residue and the mixture was cooled with ice. The crystals separated out were collected by filtration and recrystallized from a mixture of 25 ml of ethyl acetate and 250 ml of methanol to give 28.7 g of [(1R)-1-[(2R)-2-(2,4-difluorophenyl)- 2-oxiranyl]ethyl]3,5-dinitrobenzoate as colorless needles.

Fuente