Acetone → 7-fluoro-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one

HRID 510598Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 510598
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([OH:11])[CH:3]=1.[CH3:12][C:13](=O)[CH3:14].N1CCCC1>C1C=CC=CC=1.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:5]([C:8](=[O:10])[CH2:9][C:13]([CH3:14])([CH3:12])[O:11]2)=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 180AcetoneHCID 31268PyrrolidineHCID 27373264'-Fluoro-2'-hydroxyacetophenone

Produkt 1

HCID 152053737-fluoro-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-oneAusbeute 70,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To 1-(4-fluoro-2-hydroxyphenyl)ethanone (5.75 g, 37.3 mmol) and propan-2-one (12 mL, 37.3 mmol) in benzene (50 mL) was added pyrrolidine (3.11 mL, 37.3 mmol) and the reaction heated at 80° C. for 3 hours. The reaction was diluted with ethyl acetate (50 mL), washed with 1N HCl (50 mL), brine (50 mL), dried over magnesium sulfate and concentrated. The residue was purified by silica gel chromatography, eluting with a gradient of 5% ethyl acetate/hexanes to 50% ethyl acetate, to provide the title compound (5.12 g, 70.7% yield).

Aufarbeitung

  1. washwashed with 1N HCl (50 mL), brine (50 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with a gradient of 5% ethyl acetate/hexanes to 50% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-1d04325255d647dbac0a31ef4f7c9620
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096567B2

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