反应详情

To a stirring solution of 2-cyclopentylidenecyclopentan-1-one (62.5 g, 0.417 moles) in dry THF (450 mL) at room temperature under nitrogen, was added NaH (60% oil dispersion, 20.0 g, 0.5 moles) in one portion. The mixture was stirred at room temperature for 30 min and then a solution of allyl chloride (38.3 g, 0.5 moles) in THF (100 mL) was added dropwise over 30 min. When the addition was complete, the reaction was warmed gently to approximately 40° C. It was determined by TLC and GC that the reaction was complete after 18 hours. Water was added to the reaction mixture and the layers were separated, with the organic layer being washed successively with 10% HCl (aqueous), saturated NaHCO3 (aqueous), and brine. The resulting organic layer was dried with MgSO4, filtered, and concentrated. The brown oil was distilled under vacuum to give 2-cyclopent-1-enyl-2-prop-2-enylcyclopentan-1-one (54.5 g, 69.0% yield).

1. additionWhen the addition
2. temperaturethe reaction was warmed gently to approximately 40° C
3. waitwas complete after 18 hours
4. customthe layers were separated, with the organic layer
5. washbeing washed successively with 10% HCl (aqueous), saturated NaHCO3 (aqueous), and brine
6. dry with materialThe resulting organic layer was dried with MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. distillationThe brown oil was distilled under vacuum