Reaction #1714592

Reaction equation

1-bromooctane

sodium cyclopentadienide

1,3-dimethyl-2-imidazolidinone

→

n-octylcyclopentadiene

Solvents

THF

THF

THF

Conditions

Workup

1. 1
   workup.STIRRINGThe mixture was further stirred at room temperature for 24 hours
2. 2
   Temperaturewas cooled to 0° C
3. 3
   OtherThe reaction was terminated
4. 4
   workup.ADDITIONby adding 1N hydrochloric acid, and hexane
5. 5
   workup.ADDITIONwas added to the reaction liquid
6. 6
   WashThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution
7. 7
   DryingThe organic layer was dried over magnesium sulfate
8. 8
   Filtrationwas filtered
9. 9
   Concentrationwas concentrated under reduced pressure
10. 10
    workup.DISTILLATIONThe concentrate was purified by distillation under reduced pressure

Procedure

THF in a volume of 100 ml was added to 50 ml (100 mmol) of a 2 M THF solution of sodium cyclopentadienide, and the mixture was cooled to −78° C. A THF solution of 19.3 g (100 mmol) of 1-bromooctane was added thereto dropwise. Further, 11.4 g (100 mmol) of 1,3-dimethyl-2-imidazolidinone was added dropwise. The mixture was stirred at −78° C. The mixture was further stirred at room temperature for 24 hours and was cooled to 0° C. The reaction was terminated by adding 1N hydrochloric acid, and hexane was added to the reaction liquid. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and then with a saturated aqueous sodium chloride solution. The organic layer was dried over magnesium sulfate, was filtered, and was concentrated under reduced pressure. The concentrate was purified by distillation under reduced pressure to give 6.7 g (37.5 mmol) of target n-octylcyclopentadiene. The compound was identified by GC-MS. GC-MS: 178 (MS).

Source