Water → 1,4-Dioxaspiro[4.4]nonan-6-ylmethanol

HRID 31703Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 31703
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[C:11]2([CH2:15][CH2:14][CH2:13][CH:12]2[C:16](OC)=[O:17])[O:10][CH2:9][CH2:8]1.O.[OH-].[Na+]>C(OCC)C>[O:7]1[C:11]2([CH2:15][CH2:14][CH2:13][CH:12]2[CH2:16][OH:17])[O:10][CH2:9][CH2:8]1

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 10559447Methyl 1,4-dioxaspiro[4.4]nonane-6-carboxylateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 104871461,4-Dioxaspiro[4.4]nonan-6-ylmethanolAusbeute 72,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a suspension of lithium aluminum hydride (630 mg, 16.6 mmol) in diethyl ether (30 ml), methyl 1,4-dioxaspiro[4.4]nonane-6-carboxylate (3.1 g, 16.6 mmol) obtained by the method of the step (80a) above was added at 0° C. The mixture was stirred at room temperature for 3 hours. Water (0.6 ml), a 5N aqueous sodium hydroxide solution (0.6 ml), and water (1.8 ml) were sequentially added at 0° C. to the mixture and the mixture was filtrated. After water was added to the filtrate and the organic layer was separated. The aqueous layer was extracted three times with ethyl acetate. The resultant extract was dried over sodium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography (elution solvent: ethyl acetate/heptane=1/4, 1/1) to obtain the title compound (1.9 g, yield 72.4%) as a colorless oil.

Aufarbeitung

  1. customobtained by the method of the step (80a)
  2. additionabove was added at 0° C
  3. filtrationthe mixture was filtrated
  4. additionAfter water was added to the filtrate
  5. customthe organic layer was separated
  6. extractionThe aqueous layer was extracted three times with ethyl acetate
  7. extractionThe resultant extract
  8. dry with materialwas dried over sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. custompurified by silica gel column chromatography (elution solvent: ethyl acetate/heptane=1/4, 1/1)

Quellen und Nachweise

ORD-Eintrag
ord-ca25e294dd11454b8ae7a8855862d95b
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425634B2

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