Benzyl Alcohol → trans-3-Benzyloxy-4-hydroxytetrahydrofuran

HRID 370317

反応式

HRID 370317 の反応式
[O:1]1[CH:6]2[CH:2]1[CH2:3][O:4][CH2:5]2.[CH2:7]([OH:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl([O-])(=O)(=O)=O.[Mg+2].Cl([O-])(=O)(=O)=O>C(#N)C(C)C>[CH2:7]([O:14][C@H:6]1[C@H:2]([OH:1])[CH2:3][O:4][CH2:5]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

参加物

5

反応物 3

HCID 244Benzyl AlcoholHCID 24840Magnesium perchlorateHCID 675113,6-Dioxabicyclo[3.1.0]hexane

生成物 1

HCID 14307979trans-3-Benzyloxy-4-hydroxytetrahydrofuran

試薬・触媒・溶媒 1

HCID 6559Isobutyronitrile溶媒

反応条件

温度
100 °C

実験手順

To a flask fitted with a condenser and nitrogen inlet was added 3,4-epoxytetrahydrofuran (20 g, 0.23 mol), isobutyronitrile (100 ml, 5 vol), benzyl alcohol (124 g, 1.15 mol, 5 eq.) and finally magnesium perchlorate (10.3 g, 0.046 mol, 0.2 eq). The solution was heated at 100° C. for 24 hours. After cooling to room temperature, the reaction was quenched with water (1000 mL). The phases were separated and the aqueous phase was extracted with ethyl acetate (3×400 mL). After drying the organic phases over MgSO4, filtering and concentrating in vacuo, the trans-3-benzyloxy-4-hydroxytetrahydrofuran was isolated by column chromatography to give 29 g (66% yield) of a clear colorless liquid.

後処理

  1. customTo a flask fitted with a condenser and nitrogen inlet
  2. temperatureAfter cooling to room temperature
  3. customthe reaction was quenched with water (1000 mL)
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with ethyl acetate (3×400 mL)
  6. dry with materialAfter drying the organic phases over MgSO4
  7. filtrationfiltering
  8. concentrationconcentrating in vacuo

出典と根拠

ORDレコード
ord-6b610ebf91754880a244f3c223e634ad
出典データセット
uspto-grants-2000_10
特許番号
US06140516

関連ノート

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