HCID 12507349, compound → HCID 10154049, compound

HRID 728535Notes

Reaction equation

HRID 728535 reaction equation
Cl[C:2]1(Cl)[C@H:9]2[C@H:4]([CH2:5][CH2:6][CH:7]=[CH:8]2)[C:3]1=[O:10]>C(O)(=O)C.[Zn]>[C@H:9]12[CH2:2][C:3](=[O:10])[C@H:4]1[CH2:5][CH2:6][CH:7]=[CH:8]2

Participants

4

Reactant 1

HCID 12507349HCID 12507349, compound

Product 1

HCID 10154049HCID 10154049, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 1.1 g (1R,6S)-8,8-dichlorobicyclo [4.2.0]oct-2-en-7-one, prepared as shown in Example 3A, in 10 ml of glacial acetic acid was added 2.0 g of zinc dust in portions over a period of 15 minutes. The mixture was then stirred at 65° C. for 1 hour, then a further 0.5 g of zinc dust was added and the mixture stirred at 75° C. for 1 hour. The mixture was cooled, filtered, the solid washed with hexane, the filtrate and combined washings diluted with water and extracted with hexane. The hexane layer was dried over anhydrous sodium sulfate, the solvent removed under reduced pressure and the residue distilled under vacuum to give 500 mg of (1R,6S)-bicyclo[4.2.0]oct-2-en-7-one, the compound of formula (2), [α]D =+171.4°, (C=0.5, CHCl3).

Workup

  1. stirringthe mixture stirred at 75° C. for 1 hour
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. washthe solid washed with hexane
  5. additiondiluted with water
  6. extractionextracted with hexane
  7. dry with materialThe hexane layer was dried over anhydrous sodium sulfate
  8. customthe solvent removed under reduced pressure
  9. distillationthe residue distilled under vacuum

Sources & evidence

ORD record
ord-f37caa6db4b8427c961bb1301e444b7b
Source dataset
uspto-grants-1991_09
Patent number
US05049497

Reaction notes

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