Water → HCID 54348800, compound

HRID 270238Notes

Reaction equation

HRID 270238 reaction equation
[Cl:1][C:2]([Cl:14])([Cl:13])[CH2:3][CH:4](Cl)[C:5]([O:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:6].N12CCCN=C1CCCCC2.O>C1(C)C=CC=CC=1>[Cl:1][C:2]([Cl:13])([Cl:14])[CH:3]=[CH:4][C:5]([O:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11482929HCID 11482929, compound

Product 1

HCID 54348800HCID 54348800, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6 g of butyl 4,4,4,2-tetrachloro-butanoate (22.4 mmoles) in 20 ml of anhydrous toluene are charged under inert gas into a 250 ml flask and 5 ml of 1,8-diazabicyclo[5.4.0]undecan-7-ene (DBU) are added with exothermy. The mixture is brought to 60° C. for 3 hours. Upon GC control, it is observed that the reaction is complete; the mixture is cooled, water is added, the mixture is extracted with ethyl ether and anhydrified on Na2SO4. The residue obtained after evaporation of the solvent and purification by silica gel chromatography (eluant: hexane/ethyl acetate=9/1) weighs 4 g (76% yield).

Workup

  1. temperaturethe mixture is cooled
  2. extractionthe mixture is extracted with ethyl ether
  3. customThe residue obtained
  4. customafter evaporation of the solvent and purification by silica gel chromatography (eluant: hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-773c91154cef416fac4a13f6a1423cd3
Source dataset
uspto-grants-2008_11
Patent number
US07449528B2

Reaction notes

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