Triethylamine → HCID 11791389, compound

HRID 2270459Notes

Reaction equation

HRID 2270459 reaction equation
[Cl:1][C:2]1(Cl)[CH:5]([O:6][CH2:7][CH:8]([CH3:10])[CH3:9])[C:4]([Cl:12])([Cl:11])[C:3]1=[O:13].C(N(CC)CC)C.CCCCCC.C(OCC)(=O)C>COC(C)(C)C>[Cl:1][C:2]1[C:3](=[O:13])[C:4]([Cl:12])([Cl:11])[C:5]=1[O:6][CH2:7][CH:8]([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11140468HCID 11140468, compound2×HCID 21226206Ethyl acetate hexane

Product 1

HCID 11791389HCID 11791389, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution formed by dissolving 5.0 g of 2,2,4,4-tetrachloro-3-isobutoxycyclobutanone (compound (I)) and 3.6 g of triethylamine in 50 ml of tert-butyl methyl ether was refluxed for four hours. After cooling to room temperature, the solution was washed using 50 ml of 1 mol/L hydrochloric acid, and the organic layer was concentrated. The concentrated residues were separated by means of silica gel column chromatography (the composition of the developing solvent: n-hexane / ethyl acetate=100/1), to yield 3.3 g of the compound (II), 2,4,4-trichloro-3-isobutoxy-2-cyclobutene-1-one (yield=77%).

Workup

  1. customA solution formed
  2. temperaturewas refluxed for four hours
  3. washthe solution was washed
  4. concentrationthe organic layer was concentrated
  5. customThe concentrated residues were separated by means of silica gel column chromatography (the composition of the developing solvent

Sources & evidence

ORD record
ord-1669dce092304a2386f11846259f5c8f
Source dataset
uspto-grants-2001_12
Patent number
US06331653B1

Reaction notes

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