Reaktion #69258

Reaktionsgleichung

sodium hydroxide

Ethyl 1,4-dioxaspiro[4.5]dec-8-ylacetate

lithium tetrahydroaluminate

water

→

2-(1,4-Dioxaspiro[4.5]dec-8-yl)ethanol

Lösungsmittel

ether

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was cooled
2. 2
   Sonstigeadded ether (100.00 mL) and the solid that precipitated
3. 3
   Filtrationwas filtered off
4. 4
   EinengenThe filtrate was concentrated
5. 5
   Sonstigea rotary evaporator
6. 6
   Sonstigeto give the product

Vorschrift

Ethyl 1,4-dioxaspiro[4.5]dec-8-ylacetate (3.40 g, 0.0149 mol) prepared according to the procedure of Itagaki, Noriaki; Kimura, Mari; Sugahara, Tsutomu; Iwabuchi, Yoshiharu. (Organic Letters 2005; 7(19); 4181-4183.) was dissolved in ether (30.00 mL) and the mixture was cooled to 0° C. To the reaction was added 1.00 M lithium tetrahydroaluminate in ether (15.0 mL) and the resulting mixture was stirred at 0° C. for 60 minutes and at 25° C. for 2 hours. The reaction was cooled and water (0.40 mL, 0.022 mol) was added, followed by 1.00 M sodium hydroxide (0.40 mL). To the reaction was then added ether (100.00 mL) and the solid that precipitated was filtered off. The filtrate was concentrated using a rotary evaporator to give the product. 1H NMR (CDCl3): 3.94 (s, 4H), 3.67 (t, 2H), 1.20-1.80 (m, 11H).

Quelle