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

HRID 362810Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 362810
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-81319226dcc44d8a9a659ad33e62c005
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05872118

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