Ethylene Glycol → 3-(5-Benzyloxypentyl)-7,7-ethylenedioxy-cis-bicyclo-[3,3,0]oct-2-ene

HRID 2395820Notes

Reaction equation

HRID 2395820 reaction equation
C(O)CO.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:16]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]1(O)[CH2:36][C@@H:35]2[C@@H:31]([CH2:32][C:33]3([O:40][CH2:39][CH2:38][O:37]3)[CH2:34]2)[CH2:30]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[CH2:16]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]1[CH2:36][C@@H:35]2[C@@H:31]([CH2:32][C:33]3([O:37][CH2:38][CH2:39][O:40]3)[CH2:34]2)[CH:30]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 228526723-(5-Benzyloxypentyl)-7,7-ethylenedioxy-3-hydroxy-cis-bicyclo[3,3,0]octane

Product 1

HCID 228526733-(5-Benzyloxypentyl)-7,7-ethylenedioxy-cis-bicyclo-[3,3,0]oct-2-eneYield 97.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Ethylene glycol (0.05 ml) and 10 mg of p-toluenesulfonic acid were added to a solution of 209 mg of 3-(5-benzyloxypentyl)-7,7-ethylenedioxy-3-hydroxy-cis-bicyclo[3,3,0]octane (prepared as described in Preparation 9) in 2 ml of benzene, and the mixture was heated, with stirring, for 3.5 hours, whilst removing water as an azeotropic mixture. Upon completion of the reaction, the reaction mixture was neutralized with a 5% w/v aqueous solution of sodium bicarbonate. The reaction mixture was then washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off from the reaction mixture under reduced pressure, giving 193 mg of a residue. This residue was purified by silica gel column chromatography and 142 mg of the title compound were obtained as an oil from the fractions eluted with hexane containing 2-5% by volume of ethyl acetate. The product had the same properties as that of Preparation 4.

Workup

  1. temperaturethe mixture was heated
  2. customwhilst removing water as an azeotropic mixture
  3. customUpon completion of the reaction
  4. washThe reaction mixture was then washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off from the reaction mixture under reduced pressure

Sources & evidence

ORD record
ord-f44ffb98347946b4a6ceb242f40fb10f
Source dataset
uspto-grants-1996_02
Patent number
US05489613

Reaction notes

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