Carbon Dioxide → 3-{4-[(3-Fluorophenyl)methoxy]phenyl}prop-2-ynoic acid

HRID 2184354Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2184354
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[CH:14])=[CH:9][CH:8]=1.C([Li])CCC.[C:23](=[O:25])=[O:24].Cl>C1COCC1.O>[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:23]([OH:25])=[O:24])=[CH:9][CH:8]=1

Komponenten

7

Edukt 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 224766251-[(4-Ethynylphenoxy)methyl]-3-fluorobenzeneHCID 178418339Butyllithium

Produkt 1

HCID 692917433-{4-[(3-Fluorophenyl)methoxy]phenyl}prop-2-ynoic acidAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

1.93 g (8.5 mmol) of 1-(3-fluoro-benzyloxy)-4-ethynyl-benzene is dissolved in 30 ml THF and cooled to −78° C. 5.8 ml (9.4 mmol) of a 1.6 molar solution of n-butyl lithium is slowly added under stirring. The resulting solution is stirred at −78° C. for 30 minutes. An excess of solid carbon dioxide is added and the suspension is slowly allowed to warm to RT. Water is added and the mixture is acidified by addition of aqueous 0.1 molar hydrochloric acid. Extraction with ethyl acetate yields a semi-solid residue which is triturated in diethyl ether to give 1.58 g (68%) of a colorless solid. MS (neg.ions): m/e=269.1 (M−H).

Aufarbeitung

  1. stirringThe resulting solution is stirred at −78° C. for 30 minutes
  2. temperatureto warm to RT
  3. extractionExtraction with ethyl acetate
  4. customyields a semi-solid residue which
  5. customis triturated in diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-5e595702ed7b4b95a6f0abd523e25241
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06900354B2

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