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

HRID 370317

반응식

HRID 370317 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 14307979trans-3-Benzyloxy-4-hydroxytetrahydrofuran

시약·촉매·용매 1

HCID 6559Isobutyronitrile용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6b610ebf91754880a244f3c223e634ad
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06140516

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