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

HRID 370317

Reaction equation

HRID 370317 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 14307979trans-3-Benzyloxy-4-hydroxytetrahydrofuran

Reagents, catalysts & solvents 1

HCID 6559IsobutyronitrileSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6b610ebf91754880a244f3c223e634ad
Source dataset
uspto-grants-2000_10
Patent number
US06140516

Linked notes

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