Triethylamine → HCID 53919960, Verbindung

HRID 1421757Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1421757
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6]([OH:12])[CH:5]=1.CCN(CC)CC.[O:21](S(C(F)(F)F)(=O)=O)[S:22]([C:25]([F:28])([F:27])[F:26])(=O)=[O:23].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6]([O:12][S:22]([C:25]([F:28])([F:27])[F:26])(=[O:23])=[O:21])[CH:5]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 16641129Methyl 4-cyano-3-hydroxybenzoate

Produkt 1

HCID 53919960HCID 53919960, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4-cyano-3-hydroxybenzoic acid methyl ester, Example 34, Step 3 (2 g, 11.3 mmol) was dissolved in CH2Cl2 (57 ml) and cooled to 0° C. in an ice bath. The mixture was treated with Et3N (3 ml, 22.6 mmol) followed by the addition of Tf2O (1.9 ml, 11.3 mmol). The reaction mixture was warmed to room temp. and stirred for 4 hours. Saturated NaHCO3 (10 mL) was added and the mixture was extracted with EtOAc (2×10 mL). The organic layers were combined and dried (MgSO4), filtered, and concentrated. The residue was then purified by flash chromatography (15% EtOAc/Hexane) to yield the desired product.

Aufarbeitung

  1. temperatureThe reaction mixture was warmed to room temp.
  2. extractionthe mixture was extracted with EtOAc (2×10 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was then purified by flash chromatography (15% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-6db44a872c47483e9771d8ad90b7459b
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06077853

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