Hydrochloric Acid → 2(5H)-Furanone, 3-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-

HRID 357225

Reaktionsgleichung

Reaktionsgleichung von HRID 357225
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1)=O.[F:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([OH:25])=[O:24])=[CH:18][CH:17]=1.C1CCN2C(=NCCC2)CC1.Cl>C(#N)C.CCN(CC)CC>[F:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[C:23](=[O:25])[O:24][CH2:2][C:3]=2[C:5]2[CH:6]=[CH:7][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:9][CH:10]=2)=[CH:20][CH:21]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 98372-(4-Fluorophenyl)acetic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 7358232-Bromo-4'-(methylsulfonyl)acetophenone

Produkt 1

HCID 108303942(5H)-Furanone, 3-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-Ausbeute 68,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To the product of Step 1 (216 mg) dissolved in acetonitrile (4 mL) was added Et3N (0.26 mL), followed by 4-fluorophenylacetic acid (102 mg). After 1.5 h at room temperature 0.23 mL of DBU was added. The reaction mixture was stirred for another 45 min and then treated with 5 mL of 1N HCl. The product was extracted with EtOAc, dried over Na2 SO4 and concentrated. The residue was purified by flash chromatography (40% EtOAc in hexane) to yield 150 mg of the title compound as a solid.

Aufarbeitung

  1. extractionThe product was extracted with EtOAc
  2. customdried over Na2 SO4
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography (40% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-9c1fef887e114a61b1c67230af1344c0
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840746

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