Tetrahydropyran-4-ylacetic acid → 2-(Oxan-4-yl)ethan-1-ol

HRID 553589

反応式

HRID 553589 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[O:7]1[CH2:12][CH2:11][CH:10]([CH2:13][C:14](O)=[O:15])[CH2:9][CH2:8]1>C1COCC1>[O:7]1[CH2:12][CH2:11][CH:10]([CH2:13][CH2:14][OH:15])[CH2:9][CH2:8]1

参加物

4

反応物 2

HCID 2773575Tetrahydropyran-4-ylacetic acidHCID 21226445Aluminium lithium hydride

生成物 1

HCID 177509442-(Oxan-4-yl)ethan-1-ol収率 90.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of 0.55 g of LiAlH4 (13.9 mmol) in THF (10 mL) is added dropwise a solution of 2 g (13.9 mmol) of (tetrahydro-pyran-4-yl)-acetic acid in THF (10 mL) under nitrogen atmosphere (CAUTION: highly exothermic reaction!). Upon complete addition, the reaction is stirred at room temperature for 18 h. The reaction is cooled in an ice-bath and quenched with addition of 1M aqueous NH4Cl solution (2 mL). The resulting precipitate is removed by filtration through Celite® and is rinsed with ethyl acetate (3×100 mL). The filtrate is dried over Na2SO4, filtered and concentrated under reduced pressure to afford 1.63 g of 2-(tetrahydro-pyran-4-yl)-ethanol as a colorless oil. Yield: 90%; ES-MS m/z 131 [M+H].

後処理

  1. customhighly exothermic reaction
  2. additionUpon complete addition
  3. temperatureThe reaction is cooled in an ice-bath
  4. customquenched with addition of 1M aqueous NH4Cl solution (2 mL)
  5. customThe resulting precipitate is removed by filtration through Celite®
  6. washis rinsed with ethyl acetate (3×100 mL)
  7. dry with materialThe filtrate is dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-65fab71d1c714a8da636152c511b4be8
出典データセット
uspto-grants-2011_11
特許番号
US08048899B2

関連ノート

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