StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Hydrochloric Acid → 1-Methyl-3-(trifluoroMethyl)pyrazole-5-boronic acid

HRID 1859396
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1859396
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]([F:10])([F:9])[F:8])=[N:3]1.[Li+].CC([N-]C(C)C)C.C[O:20][B:21](OC)[O:22]C.Cl>C1COCC1>[CH3:1][N:2]1[C:6]([B:21]([OH:22])[OH:20])=[CH:5][C:4]([C:7]([F:10])([F:9])[F:8])=[N:3]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 2724682Lithium diisopropylamideHCID 27804041-Methyl-3-(trifluoromethyl)-1H-pyrazole

Produkt 1

HCID 120567131-Methyl-3-(trifluoroMethyl)pyrazole-5-boronic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

A solution of 1-methyl-3-trifluoromethylpyrazol (2 g) in 10 ml THF is cooled under an inert gas atmosphere to −78° C. A 2 M solution of LDA (9.75 ml) is added dropwise. The mixture is stirred to 10° C. for 1 h and cooled to −75° C. Trimethylborate (5.8 ml) is added and after stirring for 1 h at −75° C. the mixture is stirred overnight at ambient temperature. The resulting reaction solution is added to 10% hydrochloric acid (15 ml). The water phase is extracted 3 times with ethyl acetate and the combined organic phases are washed with water and a saturated sodium chloride solution. The organic phase is dried and evaporated and the residue is crystallized from water. After drying, one obtains the title compound as nearly colorless crystals (1.12 g) of mp. 138° C.

Aufarbeitung

  1. temperaturecooled to −75° C
  2. stirringafter stirring for 1 h at −75° C. the mixture
  3. stirringis stirred overnight at ambient temperature
  4. customThe resulting reaction solution
  5. extractionThe water phase is extracted 3 times with ethyl acetate
  6. washthe combined organic phases are washed with water
  7. customThe organic phase is dried
  8. customevaporated
  9. customthe residue is crystallized from water
  10. customAfter drying

Quellen und Nachweise

ORD-Eintrag
ord-b8b9c20b18d141b49324d4ebe17d2e8e
Quelldatensatz
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06528456B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion