Potassium Hydroxide → 4-(4-Fluorophenyl)oxane-4-carboxylic acid

HRID 2078074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2078074
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]([O:16]CC)=[O:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-].[K+]>CCO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]([OH:16])=[O:15])[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 67099334Ethyl 4-(4-fluorophenyl)-tetrahydro-2H-pyran-4-carboxylate

Produkt 1

HCID 64842294-(4-Fluorophenyl)oxane-4-carboxylic acidAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 19096565Water ethanolLösungsmittel

Versuchsvorschrift

A mixture of ethyl 4-(4-fluorophenyl)-tetrahydro-2H-pyran-4-carboxylate (7.1 g, 28 mmol) and KOH (3.2 g, 56 mmol) in 100 mL EtOH/H2O (4:1) was refluxed for 4 hours, M−1=223. The mixture was cooled to room temperature. The mixture was extracted with EtOAc and the organic layer discarded. The water layer was acidified with concentrated HCl, extracted with EtOAc washed with H2O and brine, dried over anhydrous Na2SO4, and concentrated in vacuo to give 4.9 g of the product as a white solid. MS (m/z)=223 (M−1)−.

Aufarbeitung

  1. temperaturewas refluxed for 4 hours
  2. extractionThe mixture was extracted with EtOAc
  3. extractionextracted with EtOAc
  4. washwashed with H2O and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0fbd8bb7cc5f4afc932d2427cb622403
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07928139B2

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