Benzene → trans-2-Decene

HRID 1584629Notes

Reaction equation

HRID 1584629 reaction equation
C(C=C)=O.O1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[CH:11]1[CH:16]=[CH:15]C=[CH:13][CH:12]=1>>[CH3:6][CH:7]=[CH:8][CH2:9][CH2:10][CH2:13][CH2:12][CH2:11][CH2:16][CH3:15]

Participants

4

Reactant 3

HCID 241BenzeneHCID 7847Acrolein2×HCID 8894Tetrahydropyran

Product 1

HCID 32899trans-2-Decene

Procedure

In this example, inverse electron demand D-A reaction of acrolein with 3,4-tetrahydropyran is described. The procedure involves refluxing of 0.056 g of acrolein, 1.68 g of tetrahydropyran and 0.30 g of the catalyst prepared according to example 1 above in 10 ml of benzene at 60 (C 20 h. The catalyst was filtered off. After evaporation of solvent, the residue was chromatographed over silica gel column by eluting with 5% acetone/petroleum ether to give 0.12 g of endo adduct, 1,9-dioxabicyclo[4.4.05,10 ]dec-2-ene

Workup

  1. customprepared
  2. customC 20 h
  3. filtrationThe catalyst was filtered off
  4. customAfter evaporation of solvent
  5. customthe residue was chromatographed over silica gel column
  6. washby eluting with 5% acetone/petroleum ether

Sources & evidence

ORD record
ord-490cabac7d5e47ccaa7ee9b756644af8
Source dataset
uspto-grants-1999_08
Patent number
US05932752

Reaction notes

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