3-Chlorocyclopent-1-ene → 3-(5-Methoxyheptyl)cyclopent-1-ene

HRID 1789519Notes

Reaction equation

HRID 1789519 reaction equation
[Mg].Cl[CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([O:10][CH3:11])[CH2:8][CH3:9].Cl[CH:13]1[CH2:17][CH2:16][CH:15]=[CH:14]1.[Cl-].[NH4+]>O1CCCC1>[CH3:11][O:10][CH:7]([CH2:8][CH3:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH:17]1[CH2:16][CH2:15][CH:14]=[CH:13]1

Participants

6

Reactant 4

HCID 72973-Chlorocyclopent-1-eneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 139240411-Chloro-5-methoxyheptane

Product 1

HCID 139240423-(5-Methoxyheptyl)cyclopent-1-ene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-25 °C

Procedure

Magnesium metal turnings (7.2 g, 0.299 moles) are added to a three-necked, round-bottomed flask equipped with a Friedrich condenser and kept under nitrogen gas. Tetrahydrofuran (300 ml) is transferred to the flask and the contents stirred. A clear, colorless solution of 1-chloro-5-methoxyheptane (48.1 g, 0.292 moles) is added portionwise and refluxed. The final third portion is added and the mixture stirred for 3 hours. The dark yellow solution is cooled to -25° C., the condenser is removed and replaced with a dry ice addition funnel. A clear solution of 3-chlorocyclopentene (29.9 g, 0.292 moles) is added over one hour. The solution is poured into a saturated ammonium chloride solution and stirred for one hour. The organic phase is separated and the aqueous phase is extracted with ether. The combined organic solutions are dried over anhydrous sodium sulfate. The solvent is removed under vacuum and the crude product is then purified by fractional distillation, yielding 3-(5-methoxyhept-1-yl)cyclopentene {3-(5-methoxyheptyl)cyclopentene} as a clear, colorless oil.

Workup

  1. customequipped with a Friedrich condenser
  2. temperaturerefluxed
  3. additionThe final third portion is added
  4. stirringthe mixture stirred for 3 hours
  5. customthe condenser is removed
  6. additionreplaced with a dry ice addition funnel
  7. stirringstirred for one hour
  8. customThe organic phase is separated
  9. extractionthe aqueous phase is extracted with ether
  10. dry with materialThe combined organic solutions are dried over anhydrous sodium sulfate
  11. customThe solvent is removed under vacuum
  12. distillationthe crude product is then purified by fractional distillation

Sources & evidence

ORD record
ord-0786b25dde1d411a93033313798ab033
Source dataset
uspto-grants-1987_08
Patent number
US04689349

Reaction notes

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