p-Toluenesulfonate → 2-Oxaspiro[4.5]dec-7-ene

HRID 280081Notes

Reaction equation

HRID 280081 reaction equation
[C:1]1([C:10]2[CH2:18][CH2:17]C[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]=2)CCCCCCNN=1.S(C1C=CC(C)=CC=1)([O-])(=O)=[O:20]>CCCCCC>[CH2:1]1[C:10]2([CH2:11][CH2:12][CH:13]=[CH:14][CH2:15]2)[CH2:18][CH2:17][O:20]1

Participants

4

Reactant 2

HCID 85570p-ToluenesulfonateHCID 66586414Diazabicylononene

Product 1

HCID 233216242-Oxaspiro[4.5]dec-7-eneYield 74%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
110 °C

Procedure

Diazabicyclononene (DBN) (76.2 g., 0.61 mole) was stirred and heated at 90° C. while the tosylate from Part E above (133.2 g. (0.43 mole)) was added portionwise. When the addition was completed the mixture was stirred at 110° C. for one hour then cooled in an ice-water bath. The mixture was then diluted with hexane causing the precipitation of salts. The resulting suspension was filtered and the solid filtered salts were washed with hexane. The hexane solution was concentrated on a rotating evaporator to a residue of 210 g. of a pale yellow liquid. This liquid was distilled to give 84.6 g. (74% yield) of the 2-oxaspiro[4.5]dec-7-ene as a relatively pure material which was not further purified.

Workup

  1. additionwas added portionwise
  2. additionWhen the addition
  3. temperaturethen cooled in an ice-water bath
  4. customthe precipitation of salts
  5. filtrationThe resulting suspension was filtered
  6. filtrationthe solid filtered salts
  7. washwere washed with hexane
  8. concentrationThe hexane solution was concentrated on a rotating evaporator to a residue of 210 g
  9. distillationThis liquid was distilled
  10. customto give 84.6 g

Sources & evidence

ORD record
ord-9ad7b3e28428474c8386e546a8d38548
Source dataset
uspto-grants-1986_05
Patent number
US04588591

Reaction notes

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