Sodium Hydroxide → HCID 68534647, Verbindung

HRID 1992861Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1992861
[CH3:1][CH:2]([CH3:19])[CH:3]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)[CH2:4][C:5]([O:7]CC)=[O:6].[OH-].[Na+]>C1COCC1.CCO>[CH3:1][CH:2]([CH3:19])[CH:3]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)[CH2:4][C:5]([OH:7])=[O:6]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 68536371HCID 68536371, Verbindung

Produkt 1

HCID 68534647HCID 68534647, VerbindungAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Ethyl 4-methyl-3-{[3-(methyloxy)phenyl]methyl}pentanoate (66) (1.72 g, 6.51 mmol) was dissolved in THF (30 mL) and EtOH (30 mL). To this solution was added 1 N NaOH (35 mL). The reaction mixture was heated at 60° C. for 1.5 h. Cooled, the mixture was extracted with EtOAc. The combined extract was washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give 1.54 g (100%) of the crude product 67 as a yellow oil. The crude product was used without further purification. 1H NMR (400 MHz, CDCl3): δ 0.91 (d, J=6.9 Hz, 3H), 0.94 (d, J=6.7 Hz, 3H), 1.70-1.80 (m, 1H), 2.10-2.25 (m, 2H), 2.32 (dd, J1=15.3 Hz, J2=6.5 Hz, 1H), 2.46 (dd, J1=13.7 Hz, J2=8.2 Hz, 1H), 2.67 (dd, J1=13.7 Hz, J2=6.4 Hz, 1H), 3.79 (s, 3H), 6.70-6.80 (m, 3H), 7.15-7.25 (m, 1H).

Aufarbeitung

  1. temperatureCooled
  2. extractionthe mixture was extracted with EtOAc
  3. extractionThe combined extract
  4. washwas washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-2f03de0ee15a45a3b99087be59387b1b
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07649093B2

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