Hydrochloric Acid → HCID 18182605, Verbindung

HRID 1264216Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1264216
C[O:2][C:3](=[O:18])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)=[CH:9][CH:8]=1)([CH3:6])[CH3:5].[OH-].[Na+].Cl>CO.C1COCC1.CCOCC>[O:14]1[CH:15]=[CH:16][CH:17]=[C:13]1[C:10]1[CH:11]=[CH:12][C:7]([C:4]([CH3:6])([CH3:5])[C:3]([OH:18])=[O:2])=[CH:8][CH:9]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21350305HCID 21350305, Verbindung

Produkt 1

HCID 18182605HCID 18182605, VerbindungAusbeute 94,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 21899815MeOH tetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a solution of 2-(4-(furan-2-yl)-phenyl)-2-methyl-propionic acid methyl ester (2.0 g, 8.2 mmol) (reference example 30a) in MeOH/THF (20 mL, 1/1) is added NaOH (2 mL, 6M). The resulting solution is stirred for 1 hour then heated to 65° C. and stirred at this temperature for 2 hours. The reaction mixture is then cooled and acidified (to pH 1) with hydrochloric acid (2 M). The resulting mixture is diluted with ether, washed with water and brine, dried over MgSO4 and concentrated to give 1.78 g of the title compound as a solid. 1H NMR (CDCl3) d 1.61 (s, 6H), 6.45 (dd, J 3, 2 Hz, 1H), 6.62 (d, J=3 Hz, 1H), 7.42 (m, 2H), 7.45 (d, J=2 Hz, 1H), 7.64 (m, 2H). MS (EI) m/z 230 (M+)

Aufarbeitung

  1. stirringstirred at this temperature for 2 hours
  2. temperatureThe reaction mixture is then cooled
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e5dc483d59ff42a4b9e6ce97da87d3e7
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06541505B1

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