Реакция #59981

Уравнение реакции

lithium aluminum hydride

methyl 1,4-dioxaspiro[4.4]nonane-6-carboxylate

Water

sodium hydroxide

water

→

title compound

Выход 72.4%

1,4-dioxaspiro[4.4]non-6-ylmethanol

Выход 72.4%

Растворители

diethyl ether

Условия реакции

Обработка

1. 1
   Другоеobtained by the method of the step (80a)
2. 2
   workup.ADDITIONabove was added at 0° C
3. 3
   Фильтрацияthe mixture was filtrated
4. 4
   workup.ADDITIONAfter water was added to the filtrate
5. 5
   Другоеthe organic layer was separated
6. 6
   ЭкстракцияThe aqueous layer was extracted three times with ethyl acetate
7. 7
   ЭкстракцияThe resultant extract
8. 8
   Сушкаwas dried over sodium sulfate
9. 9
   Концентрированиеconcentrated under reduced pressure
10. 10
    Другоеpurified by silica gel column chromatography (elution solvent: ethyl acetate/heptane=1/4, 1/1)

Методика

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.

Источник