1-Acetylnaphthalene → (1R)-1-(Naphthalen-1-yl)ethan-1-ol

HRID 1358714Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1358714
[OH-].[K+].CC(O)C.[C:7]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)(=[O:9])[CH3:8].[H][H]>CC(O)C>[C:10]1([C@H:7]([OH:9])[CH3:8])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1

Komponenten

5

Edukt 3

HCID 136631-AcetylnaphthaleneHCID 23443544KOH isopropanolHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 6976567(1R)-1-(Naphthalen-1-yl)ethan-1-olAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

To 100 mL of an autoclave was fed 11.7 mg (0.010 mmol) of RuCl2[(S)-binap][(S)-binaphthyldiamine]. After purging with argon, 2.8 mL of 2-propanol and 50 μL (0.025 mmol) of KOH/2-propanol (0.5M solution) were added. The resulting mixture was stirred at room temperature for 30 minutes. After addition of 0.38 mL (2.5 mmol) of 1′-acetonaphthone, stirring was conducted at room temperature for 4 hours at a hydrogen pressure adjusted to 0.8 Mpa. The reaction mixture was concentrated by distilling off the solvent under reduced pressure. The residue was filtered using silica gel, whereby 202 mg (yield: 47%) of (R)-1-(1-naphthyl)ethanol was obtained. The enantio-selectivity was 30%ee.

Aufarbeitung

  1. additionwere added
  2. stirringstirring
  3. concentrationThe reaction mixture was concentrated
  4. distillationby distilling off the solvent under reduced pressure
  5. filtrationThe residue was filtered

Quellen und Nachweise

ORD-Eintrag
ord-83ae7b03f68a41a8b1780938c1be3850
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06596887B2

Notizen zur Reaktion

Wird geladen…