Diethyl Ether → 2,2-Dichloro-3-oxocyclobutyl pivalate

HRID 1697216Notes

Reaction equation

HRID 1697216 reaction equation
[C:1](OC=C)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].Cl[C:11]([Cl:16])([Cl:15])[C:12](Cl)=[O:13].[O-][Mn](=O)(=O)=O.[K+].[CH3:23][CH2:24][O:25]CC>[Zn]>[C:1]([O:13][CH:12]1[CH2:23][C:24](=[O:25])[C:11]1([Cl:16])[Cl:15])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 6420Trichloroacetyl chlorideHCID 256591Vinyl pivalateHCID 516875Potassium Permanganate

Product 1

HCID 575158702,2-Dichloro-3-oxocyclobutyl pivalate

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Conditions

Temperature
22.5 °C

Procedure

To a stirred mixture of vinyl pivalate (30 g, 234 mmol) and zinc (31 g, 468 mmol) in ether (300 ml) was added a solution of 2,2,2-trichloroacetyl chloride (55 g, 304 mmol) in ether (300 ml) dropwise (2-3 h) in a water bath. (Note: fast addition causes the reaction temp to elevate) while maintaining the reaction temperature between 15-30° C. After the reaction was done (stained with KMnO4 solution), it was filtered through Celite. The filtrate was washed with cold water, brine, dried over MgSO4 and concentrated to give the title compound as an orange solid.

Workup

  1. addition(Note: fast addition
  2. customthe reaction temp
  3. filtrationwas filtered through Celite
  4. washThe filtrate was washed with cold water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-418e98bfb3174ebea6398733dd17ea66
Source dataset
uspto-grants-2012_04
Patent number
US08163909B2

Reaction notes

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