2,2-Dichloro-3-oxocyclobutyl pivalate → 3-Oxocyclobutyl pivalate

HRID 1039688Notes

Reaction equation

HRID 1039688 reaction equation
[C:1]([O:7][CH:8]1[CH2:11][C:10](=[O:12])[C:9]1(Cl)Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]>CC(O)=O.[Zn]>[C:1]([O:7][CH:8]1[CH2:11][C:10](=[O:12])[CH2:9]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 575158702,2-Dichloro-3-oxocyclobutyl pivalate

Product 1

HCID 533969923-Oxocyclobutyl pivalate

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×

Procedure

To a stirred suspension of zinc dust (103 g, 1568 mmol) in HOAc (200 ml) was added a solution of 2,2-dichloro-3-oxocyclobutyl pivalate (75 g, 314 mmol) in HOAc (400 ml) dropwise in an ice bath. The reaction mixture was stirred for 1 h, filtered the solid through celite and washed with DCM. The DCM layer was washed with H2O, NaHCO3, brine, dried over MgSO4, filtered and concentrated. The crude material was purified by ISCO (10% EtOAc/Hexanes) to give the title compound as a light yellow oil.

Workup

  1. filtrationfiltered the solid through celite
  2. washwashed with DCM
  3. washThe DCM layer was washed with H2O, NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by ISCO (10% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-0b2e31a489e347f68e0074489dd476fa
Source dataset
uspto-grants-2013_10
Patent number
US08552181B2

Reaction notes

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