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

HRID 1645648ノート

反応式

HRID 1645648 の反応式
[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

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 10559447Methyl 1,4-dioxaspiro[4.4]nonane-6-carboxylateHCID 21226445Aluminium lithium hydride

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-83fdb475509c4f9cb9701ae2b6ffde18
出典データセット
uspto-grants-2012_02
特許番号
US08124780B2

反応ノート

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