Ethylene Glycol → HCID 86734468, compound

HRID 435954Notes

Reaction equation

HRID 435954 reaction equation
[CH3:1][C:2]([CH3:27])([CH2:23][CH2:24][CH2:25][CH3:26])[C:3](=[O:22])[CH:4]=[CH:5][C@@H:6]1[CH2:10][CH2:9][C:8](=[O:11])[C@H:7]1[CH2:12][CH:13]=[CH:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19].[CH2:28](O)[CH2:29][OH:30].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:28]1[CH2:29][O:30][CH:9]2[CH:8]([CH:7]([CH2:12]/[CH:13]=[CH:14]/[CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:6](/[CH:5]=[CH:4]\[CH:3]([OH:22])[C:2]([CH3:27])([CH3:1])[CH2:23][CH2:24][CH2:25][CH3:26])[CH2:10]2)[O:11]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 70618039HCID 70618039, compound

Product 1

HCID 86734468HCID 86734468, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of the compound of formula 3 in which L is the radical C, methyl trans-7-[2-(4,4-dimethyl-3-oxo-1-octenyl)-5-oxo-cyclopentyl]-5-heptenoate (2.5 g, γmaxfilm 1730-1725, 1667, 1620 cm-1), ethylene glycol (360 mg) and p-toluenesulfonic acid (35 mg) in 50 ml of benzene is heated at reflux for 2.5 hr. Thereafter the mixture is extracted with ether. The ether extract is washed with water, dried (MgSO4) and concentrated under reduced pressure. The residue containing methyl trans, cis-7-[2-(ethylenedioxy)-5-(4,4-dimethyl-3-oxo-1-octenyl)cyclopentyl-5-heptenoate, γmaxfilm 1730, 1667, 1620 cm-1, is taken up in 20 ml of methanol and treated with sodium borohydride (350 mg) in small portions with stirring which is continued for 30 minutes. The solvent is evaporated under reduced pressure, the residue taken up in ether, washed to neutrality with water, dried (MgSO4) and the solvent concentrated under reduced pressure. The residue is chromatographed on silica gel (140 g). Elution with ethyl acetate-benzene (4:1) and concentration of the eluant affords methyl trans,cis-7-[2-(ethylenedioxy)-5-(3-hydroxy-4,4-dimethyl-1-octenyl)cyclopentyl]-5-heptenoate, γmaxfilm 3460, 1740, 950 cm-1.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 2.5 hr
  3. extractionThereafter the mixture is extracted with ether
  4. extractionThe ether extract
  5. washis washed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. additionThe residue containing methyl trans, cis-7-[2-(ethylenedioxy)-5-(4,4-dimethyl-3-oxo-1-octenyl)cyclopentyl-5-heptenoate, γmaxfilm 1730, 1667, 1620 cm-1
  9. additiontreated with sodium borohydride (350 mg) in small portions
  10. customThe solvent is evaporated under reduced pressure
  11. washwashed
  12. dry with materialdried (MgSO4)
  13. concentrationthe solvent concentrated under reduced pressure
  14. customThe residue is chromatographed on silica gel (140 g)
  15. washElution with ethyl acetate-benzene (4:1) and concentration of the eluant

Sources & evidence

ORD record
ord-205913cbe32945c6bf3697c5096c9ea1
Source dataset
uspto-grants-1977_02
Patent number
US04007171

Reaction notes

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