(RS)-3-benzyl-2,2-dichlorocyclobutanone → 3-Benzylcyclobutan-1-one

HRID 1280749Notes

Reaction equation

HRID 1280749 reaction equation
[CH2:1]([CH:8]1[CH2:11][C:10](=[O:12])[C:9]1(Cl)Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[CH2:1]([CH:8]1[CH2:11][C:10](=[O:12])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 18425787(RS)-3-benzyl-2,2-dichlorocyclobutanone

Product 1

HCID 5760853-Benzylcyclobutan-1-oneYield 76.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of (RS)-3-benzyl-2,2-dichlorocyclobutanone (0.3 g. 1.3 mmol) in acetic acid (3 ml) was refluxed for 1 hour in the presence of zinc (0.86 g, 13.1 mmol. powder). The reaction mixture was cooled to room temperature and filtered over decalite. The filtrate was neutralized with saturated NaHCO3. The organic phase was washed successively with H2O and brine, dried over Na2SO4, and concentrated. The residue was chromatographed over silica gel (hexane-ethylacetate 4:1) to provide 3-benzyl-cyclobutanone (0.16 g, 76%) as a colorless oil, MS: m/e=160.2 (M+).

Workup

  1. filtrationfiltered over decalite
  2. washThe organic phase was washed successively with H2O and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was chromatographed over silica gel (hexane-ethylacetate 4:1)

Sources & evidence

ORD record
ord-69477ef5ca224a1eb14a46662bd7105d
Source dataset
uspto-grants-2002_09
Patent number
US06451819B2

Reaction notes

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