Trifluoroacetic acid → (E)-2-(6-fluoro-1-indanylidene)acetic acid

HRID 1954857Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1954857
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][CH2:14][C:15]2([CH2:19][C:20]([O-:22])=[O:21])O)=[CH:11][CH:10]=1.[Li+]>ClCCl>[F:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][CH2:14]/[C:15]/2=[CH:19]\[C:20]([OH:22])=[O:21])=[CH:11][CH:10]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 23678141Lithium 2-(6-fluoro-1-hydroxy-1-indanyl)acetate

Produkt 1

HCID 70130971(E)-2-(6-fluoro-1-indanylidene)acetic acidAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (1.5 mL) was added to a stirred, chilled (ice-methanol bath) suspension of lithium 2-(6-fluoro-1-hydroxy-1-indanyl)acetate (0.5 g, 2.3 mmol) in dichloromethane (13.5 mL). After 15 min, the mixture was concentrated in vacuo and the resulting white solid was recrystallized from aqueous acetone to give (E)-2-(6-fluoro-1-indanylidene)acetic acid as white crystals (0.32 g, 73%) identical to compound of Example 1i by mixed m.p., (203-205° C.) and NMR;

Aufarbeitung

  1. temperaturechilled
  2. concentrationthe mixture was concentrated in vacuo
  3. customthe resulting white solid was recrystallized from aqueous acetone

Quellen und Nachweise

ORD-Eintrag
ord-c9a860195fdc4bf28b6b1b143ef9f842
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06124284

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