Water → HCID 82012920, Verbindung

HRID 1771804Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1771804
[C:1]([C:3]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]([F:14])[C:4]=1C(O)=O)#[N:2].CC[N:17](CC)CC.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.O>C1COCC1>[NH2:17][C:4]1[C:8]([F:14])=[CH:9][CH:10]=[C:11]([O:12][CH3:13])[C:3]=1[C:1]#[N:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 834105191427408-14-7

Produkt 1

HCID 82012920HCID 82012920, VerbindungAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-cyano-6-fluoro-3-methoxy-benzoic acid (2 g, 10.3 mmol, 1.0 eq) in THF (40 mL) were added Et3N (3.6 mL, 25.8 mmol, 2.5 eq) and DPPA (2.97 g, 10.8 mmol, 1.05 eq). The reaction was stirred at room temperature 3 h then water (10 mL) was added and the mixture was heated at reflux for 2 h. The THF was removed in vacuo and the aqueous solution diluted with water and extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether:EtOAc, 5:1) to give the title compound as an off-white solid (900 mg, 53%).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 h
  3. customThe THF was removed in vacuo
  4. additionthe aqueous solution diluted with water
  5. extractionextracted with EtOAc
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe residue obtained
  11. customwas purified by column chromatography (petroleum ether:EtOAc, 5:1)

Quellen und Nachweise

ORD-Eintrag
ord-2800b420d0a2492386183b8acda967cc
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249085B2

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