Réaction #59985

Équation de réaction

lithium aluminum hydride

sodium hydroxide

ethyl 4-cyclohexanonecarboxylate

ethylene glycol

→

title compound

Rendement 85.1%

1,4-dioxaspiro[4.5]dec-8-ylmethanol

Rendement 85.1%

Solvants

tetrahydrofuran

tetrahydrofuran

water

water

water

benzene

Conditions de réaction

Traitement

1. 1
   Autreseparator was attached to a round bottom flask
2. 2
   TempératureThe mixture was heated
3. 3
   Températureunder reflux for 3 hours
4. 4
   Concentrationthe mixture was concentrated
5. 5
   SéchageAfter dried over sodium sulfate
6. 6
   Filtrationthe mixture was filtrated
7. 7
   ConcentrationThe filtrate was concentrated under reduced pressure
8. 8
   Autrepurified by silica gel column chromatography (elution solvent: ethyl acetate/heptane=1/2, 1/1, 2/1)

Mode opératoire

A reflux condenser equipped with a Dean-Stark water separator was attached to a round bottom flask containing ethyl 4-cyclohexanonecarboxylate (5 ml, 31.4 mmol), ethylene glycol (1.93 ml, 34.5 mmol), p-toluenesulfonic acid monohydrate (200 mg, 1.05 mmol), and benzene (30 ml). The mixture was heated under reflux for 3 hours. To the reaction mixture, triethylamine (181 μl, 1.3 mmol) was added and the mixture was concentrated. A tetrahydrofuran solution of the resultant crude substance was added to a tetrahydrofuran (30 ml) suspension of lithium aluminum hydride (1.31 g, 34.5 mmol) at 0° C. After the mixture was stirred at room temperature for 7 hours, water (1.3 ml), a 5N aqueous sodium hydroxide solution (1.3 ml), and water (3.9 ml) were sequentially added to the mixture at 0° C. After dried over sodium sulfate, the mixture was filtrated. The filtrate was 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 (4.6 g, yield: 85.1%) as a colorless oil.

Source