Methanol → HCID 57467467, Verbindung

HRID 1890794Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1890794
[F:1][C:2]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:3]=1[O:4][C:5]([CH3:10])([CH3:9])[C:6]([NH2:8])=O.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.CO>C(Cl)Cl>[F:1][C:2]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:3]=1[O:4][C:5]([CH3:10])([CH3:9])[C:6]#[N:8]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 57467466HCID 57467466, Verbindung

Produkt 1

HCID 57467467HCID 57467467, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of Example 51A (0.9 g, 4.0 mmol) in methylene chloride (10 mL) and triethylamine (2.2 mL, 15.8 mmol) was added 2,2,2-trifluoroacetic anhydride (1.6 mL, 11.9 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for three hours before methanol was added to quench the reaction. The reaction mixture was washed with saturated aqueous NaHCO3 solution, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-100% methanol/ethyl acetate(1/10) in hexanes) to obtain the titled compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.71 (s, 6H), 7.08-7.18 (m, 1H), 7.36-7.49 (m, 2H).

Aufarbeitung

  1. additionwas added
  2. customto quench
  3. customthe reaction
  4. washThe reaction mixture was washed with saturated aqueous NaHCO3 solution
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-44c437e655ad4dc0b5c70ea3c452657a
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507493B2

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