Hydrochloric Acid → 2-Ethyl-6-fluoro-3-phenyl-4H-chromen-4-one

HRID 1484296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1484296
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:17])=[C:6]([C:8](=[O:16])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=1.[C:18](OC(=O)CC)(=O)[CH2:19][CH3:20].Cl>C(N(CC)CC)C>[CH2:19]([C:20]1[O:17][C:5]2[C:6]([C:8](=[O:16])[C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH3:18]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 31263Propionic anhydrideHCID 27785851-(5-Fluoro-2-hydroxyphenyl)-2-phenylethanone

Produkt 1

HCID 602090512-Ethyl-6-fluoro-3-phenyl-4H-chromen-4-oneAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Intermediate 50 (3.0 g, 13.63 mmoles) was taken in a RB flask and to this triethylamine (30 ml) and propionic anhydride (5.30 g, 40.78 mmoles) were added and the mixture was refluxed for 24 h. After cooling to RT, the reaction mixture was acidified by the addition of 1N HCl solution, extracted with ethyl acetate, washed with sodium bicarbonate solution, dried with sodium sulphate and concentrated. The crude product was purified by column chromatography with ethyl acetate:petroleum ether to afford the title compound as off-white solid (2.27 g, 65% yield). 1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 7.79 (dd, J=7.1, 4.4 Hz, 1H), 7.73 (dt, J=7.7, 3.1 Hz, 2H), 7.46 (t, J=8.2 Hz, 2H), 7.40 (m, 1H), 7.27 (dd, J=8.2, 1.4 Hz, 2H), 2.55 (q, J=7.5 Hz, 2H), 1.19 (t, J=7.6 Hz, 3H).

Aufarbeitung

  1. additionwere added
  2. temperaturethe mixture was refluxed for 24 h
  3. extractionextracted with ethyl acetate
  4. washwashed with sodium bicarbonate solution
  5. dry with materialdried with sodium sulphate
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-954b098d29d446ae9a5eca0a7525815f
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09421209B2

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