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

HRID 862759Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 862759
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-a9c0a3bbdec346c38fe140bf4a089175
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05719186

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