Ethyl 2-(1,4-dioxaspiro[4.5]decan-8-yl)acetate → 2-(1,4-Dioxaspiro(4.5)decan-8-yl)ethan-1-ol

HRID 1404397

Reaktionsgleichung

Reaktionsgleichung von HRID 1404397
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][C:12](OCC)=[O:13])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][OH:13])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 15700391Ethyl 2-(1,4-dioxaspiro[4.5]decan-8-yl)acetateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 118054582-(1,4-Dioxaspiro(4.5)decan-8-yl)ethan-1-olAusbeute 102,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of ethyl 2-(1,4-dioxaspiro[4.5]decan-8-yl)acetate from Step 1 (3.31 g, 14.5 mmol) in Et2O (80 mL) at 0° C. under N2 was added LiAlH4 (1M in THF, 13.66 mL, 13.66 mmol) in 15 min. The resulting mixture was stirred at 0° C. for another 20 min and quenched by addition of saturated aqueous NH4Cl solution, extracted with EtOAc, dried over Na2SO4. Filtration and evaporation to dryness gave the alcohol as white solid (2.76 g, 100%). LC/MC: 187.1 (MH)

Aufarbeitung

  1. customquenched by addition of saturated aqueous NH4Cl solution
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationFiltration and evaporation to dryness

Quellen und Nachweise

ORD-Eintrag
ord-590d9d7fa83f48b487923e4be701d69d
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912169B2

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