Potassium Hydroxide → 1-(4-Fluorophenyl)-3-(3,4-methylenedioxyphenyl)indane-2-carboxylic acid

HRID 399212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 399212
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]([C:17]3[CH:22]=[CH:21][C:20]4[O:23][CH2:24][O:25][C:19]=4[CH:18]=3)[CH:9]2[C:26]([O:28]CC)=[O:27])=[CH:4][CH:3]=1.[OH-].[K+]>CCO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]([C:17]3[CH:22]=[CH:21][C:20]4[O:23][CH2:24][O:25][C:19]=4[CH:18]=3)[CH:9]2[C:26]([OH:28])=[O:27])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 67643878Ethyl(1RS,2RS,3SR)-1-(4-Fluorophenyl)-3-(3,4-methylenedioxyphenyl)indane-2-carboxylate

Produkt 1

HCID 159085011-(4-Fluorophenyl)-3-(3,4-methylenedioxyphenyl)indane-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of ethyl (1RS,2RS,3SR)-1-(4-fluorophenyl)-3-(3,4-methylenedioxyphenyl)indane-2-carboxylate (60 mg, 0.15 mmol) in EtOH (0.5 ml) was added 6M KOH (0.14 ml, 0.84 mmol). The resulting mixture was allowed to stir at room temperature overnight, then was concentrated under reduced pressure. The residue was partitioned between H2O and Et2O. The aqueous phase was acidified with 3M HCl and extracted several times with EtOAc. The combined EtOAc extracts were washed successively with H2O and saturated aqueous NaCl and dried (MgSO4). The solvent was removed in vacuo to afford an oil, which was crystallized from EtOAc/hexanes. The title compound was obtained as an off-white crystalline solid (22 mg, 39%); m.p. 146°-149° C.

Aufarbeitung

  1. concentrationwas concentrated under reduced pressure
  2. customThe residue was partitioned between H2O and Et2O
  3. extractionextracted several times with EtOAc
  4. washThe combined EtOAc extracts were washed successively with H2O and saturated aqueous NaCl
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo
  7. customto afford an oil, which
  8. customwas crystallized from EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-77bc52738ebf4b1bbf51037e1c86b6d2
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05817693

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