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

HRID 1358712Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1358712
[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 98,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A 100 mL autoclave was charged with 11.7 mg (0.010 mmol) of the mixture of RuCl2[(S)-dm-binap][(S,S)-dpen] and RuCl2[(R)-dm-binap][(R)-3,3′-dimethyl-1,1′-binaphthyl-2,2′-diamine] obtained in Example 2. 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 420 mg (yield: 98.7%) of (R)-1-(1-naphthyl)ethanol was obtained. The enantio-selectivity was 96.2%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-b5b29684a265427b8ff2572f88c0c997
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06596887B2

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