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 1789534Notes

Reaction equation

HRID 1789534 reaction equation
Cl[C:2]1(Cl)[C:8](=[O:9])[CH:7]2[CH:3]1[CH2:4][CH2:5][CH:6]2[CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([O:17][CH3:18])[CH2:15][CH3:16]>C(O)(=O)C.[Zn]>[CH3:18][O:17][CH:14]([CH2:15][CH3:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH:6]1[CH2:5][CH2:4][CH:3]2[CH:7]1[C:8](=[O:9])[CH2:2]2

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 (3 g) is added to a stirred solution of 6,6-dichloro-2(5-methoxyhept-1-yl)bicyclo[3.2.0]heptan-7-one {7,7-dichloro-4(5-methoxyheptyl)bicyclo[3.2.0]heptan-6-one} (2 g, 6 moles) in acetic acid (100 ml) under a nitrogen atmosphere. The solution is stirred at room temperature for one hour, then refluxed for 13 hours, 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 2-(5-methoxyhept-1-yl)bicyclo[3.2.0]heptan-7-one {4-(5-methoxyheptyl) bicyclo[3.2.0]heptan-6-one} (1.2 g).

Workup

  1. temperaturerefluxed for 13 hours
  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-a0fb30ee3b2c41b0b02c77836884e130
Source dataset
uspto-grants-1987_08
Patent number
US04689349

Reaction notes

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