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

HRID 1921945Notes

Reaction equation

HRID 1921945 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-4e95d057b5eb423884162b8fcc8c1ca1
Source dataset
uspto-grants-2012_05
Patent number
US08173810B2

Reaction notes

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