Water → HCID 18699436, Verbindung

HRID 377656

Reaktionsgleichung

Reaktionsgleichung von HRID 377656
[C:1]([C:3]1[C:7](I)=[CH:6][N:5]([C:9]2[C:14]([Cl:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=2[Cl:20])[N:4]=1)#[N:2].C([Li])CCC.[F:26][C:27]([F:39])([F:38])[C:28]([F:37])([F:36])[C:29]([F:35])([F:34])[C:30](OC)=[O:31].O>O1CCCC1>[C:1]([C:3]1[C:7]([C:30](=[O:31])[C:29]([F:34])([F:35])[C:28]([F:36])([F:37])[C:27]([F:39])([F:38])[F:26])=[CH:6][N:5]([C:9]2[C:14]([Cl:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=2[Cl:20])[N:4]=1)#[N:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 67741Methyl 2,2,3,3,4,4,4-heptafluorobutanoateHCID 211881263-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodopyrazoleHCID 178418339Butyllithium

Produkt 1

HCID 18699436HCID 18699436, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-73 °C

Versuchsvorschrift

To a stirred solution of 3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodopyrazole (3.0 g) in tetrahydrofuran (80 ml) at -80° C. under an atmosphere of nitrogen was added, at such a rate that the temperature of the reaction mixture did not exceed -73° C., n-butyllithium (2.78 ml of a 2.5M solution in hexanes). The mixture was stirred at -73° C. for 10 minutes and then a solution of methyl heptafluorobutyrate (1.07 ml) in tetrahydrofuran (5 ml) was then added at such a rate that the temperature of the reaction mixture did not exceed -75° C. Upon completion of the addition the mixture allowed to warm to room temperature over a period of 1.5 hours. Water (100 ml) was added and the mixture extracted twice with ethyl acetate (50 ml). The combined organic layers were dried (Na2SO4) and evaporated to give a pale yellow solid which was purified by column chromatography on silica gel (150 g) eluted with ether:hexane (3:2). Combination and evaporation of suitable fractions gave a yellow oil which was further purified by column chromatography on silica gel (150 g) eluted initially with hexane:ether (19:1), then hexane:ether (9:1) and finally hexane:ether (1:1). Combination and evaporation of suitable fractions gave the title compound as a pale yellow solid, m.p. 102-103° C.

Aufarbeitung

  1. customdid not exceed -73° C.
  2. customdid not exceed -75° C
  3. additionUpon completion of the addition the mixture
  4. temperatureto warm to room temperature over a period of 1.5 hours
  5. extractionthe mixture extracted twice with ethyl acetate (50 ml)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. customevaporated
  8. customto give a pale yellow solid which
  9. customwas purified by column chromatography on silica gel (150 g)
  10. washeluted with ether:hexane (3:2)
  11. customCombination and evaporation of suitable fractions
  12. customgave a yellow oil which
  13. customwas further purified by column chromatography on silica gel (150 g)
  14. washeluted initially with hexane:ether (19:1)
  15. customCombination and evaporation of suitable fractions

Quellen und Nachweise

ORD-Eintrag
ord-0d36837ce02d4d2c924a8226743e7245
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06028096

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