Water → HCID 15304482, compound

HRID 1266002Notes

Reaction equation

HRID 1266002 reaction equation
[C:1]1(=[C:6]2[CH2:10][CH2:9][CH2:8][C:7]2=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:14](Cl)[CH:15]=[CH2:16].O>C1COCC1>[C:1]1([C:6]2([CH2:16][CH:15]=[CH2:14])[CH2:10][CH2:9][CH2:8][C:7]2=[O:11])[CH2:2][CH2:3][CH2:4][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7850Allyl chlorideHCID 24758Sodium hydrideHCID 69995Cyclopentylidenecyclopentan-2-one

Product 1

HCID 15304482HCID 15304482, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-62dac055f7f047679bc8ad1d6c93b823
Source dataset
uspto-grants-2003_04
Patent number
US06548474B1

Reaction notes

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