7,7-Dichloro-4-(5-methoxyheptyl)bicyclo[3.2.0]heptan-6-one → 2-(5-Methoxyhept-1-yl)bicyclo[3.2.0]heptan-7-one

HRID 569219Notes

Reaction equation

HRID 569219 reaction equation
Cl[C:2]1(Cl)[CH:8]2[CH:4]([CH:5]([CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([O:16][CH3:17])[CH2:14][CH3:15])[CH2:6][CH2:7]2)[C:3]1=[O:18]>C(O)(=O)C.[Zn]>[CH3:17][O:16][CH:13]([CH2:14][CH3:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH:5]1[CH:4]2[CH:8]([CH2:2][C:3]2=[O:18])[CH2:7][CH2:6]1

Participants

4

Reactant 1

HCID 139240447,7-Dichloro-4-(5-methoxyheptyl)bicyclo[3.2.0]heptan-6-one

Product 1

HCID 142040962-(5-Methoxyhept-1-yl)bicyclo[3.2.0]heptan-7-one

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc (4 g) is added to a stirred solution of 7,7-dichloro-4-(5-methoxyheptyl)bicyclo[3.2.0]heptan-6-one (2 g) in glacial acetic acid (120 ml). The solution is stirred at room temperature for one hour, then refluxed for 1 hour, after which time the mixture is filtered through a sintered glass funnel and the ether solution dried over anhydrous sodium sulfate. The solvent is removed under vacuum, leaving the crude product. Chromatography on silica gel yields 4-(5-methoxyheptyl)bicyclo [3.2.0]heptan-6-one (Formula IV, X=--(CH2)4 --CH(OCH3)--C2H5).

Workup

  1. temperaturerefluxed for 1 hour
  2. filtrationafter which time the mixture is filtered through a sintered glass funnel
  3. dry with materialthe ether solution dried over anhydrous sodium sulfate
  4. customThe solvent is removed under vacuum
  5. customleaving the crude product

Sources & evidence

ORD record
ord-c231673469904954af31e8fcec00da3c
Source dataset
uspto-grants-1988_03
Patent number
US04731458

Reaction notes

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