Water → 3,3-Dimethyl-1,5-dioxaspiro[5.5]undecan-9-ol

HRID 31705

Reaktionsgleichung

Reaktionsgleichung von HRID 31705
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([CH3:20])[CH2:19][O:18][C:11]2([CH2:17][CH2:16][C:14](=[O:15])[CH2:13][CH2:12]2)[O:10][CH2:9]1.O.[OH-].[Na+]>O1CCCC1>[CH3:7][C:8]1([CH3:20])[CH2:9][O:10][C:11]2([CH2:12][CH2:13][CH:14]([OH:15])[CH2:16][CH2:17]2)[O:18][CH2:19]1

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 5879683,3-Dimethyl-1,5-dioxaspiro(5.5)undecan-9-oneHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 124700963,3-Dimethyl-1,5-dioxaspiro[5.5]undecan-9-olAusbeute 91,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To the suspension of lithium aluminum hydride (748 mg, 19.7 mmol) in tetrahydrofuran (40 ml), a tetrahydrofuran solution of 1,4-cyclohexanedione mono-2,2-dimethyltrimethylene ketal (3.9 g, 19.7 mmol) was added at 0° C. The mixture was stirred at room temperature for 3 hours. After water (0.7 ml), a 5N aqueous sodium hydroxide solution (0.7 ml), and water (2.1 ml) were sequentially added at 0° C. to the mixture, the mixture was dried over sodium sulfate, filtrated, concentrated under reduced pressure, and purified by silica gel column chromatography (elution solvent: ethyl acetate/heptane=1/2, 1/1, 2/1) to obtain the title compound (3.6 g, yield: 91.2%) as a colorless oil.

Aufarbeitung

  1. dry with materialthe mixture was dried over sodium sulfate
  2. filtrationfiltrated
  3. concentrationconcentrated under reduced pressure
  4. custompurified by silica gel column chromatography (elution solvent: ethyl acetate/heptane=1/2, 1/1, 2/1)

Quellen und Nachweise

ORD-Eintrag
ord-1ffbaa88e08e4ae99cd7446a52d0d5c7
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425634B2

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