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

HRID 1645648노트

반응식

HRID 1645648 반응식
[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

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 10559447Methyl 1,4-dioxaspiro[4.4]nonane-6-carboxylateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 104871461,4-Dioxaspiro[4.4]nonan-6-ylmethanol수율 72.4%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-83fdb475509c4f9cb9701ae2b6ffde18
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124780B2

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