Hexachloroethane → HCID 66961006, compound

HRID 1362692Notes

Reaction equation

HRID 1362692 reaction equation
C1COCC1.[O:6]1[CH2:10][CH2:9][O:8][CH:7]1[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)=[C:13]([O:22][CH3:23])[CH:12]=1.C([Li])CCC.[Cl:29]C(Cl)(Cl)C(Cl)(Cl)Cl>C(OCC)(=O)C.O>[Cl:29][C:18]1[N:17]([C:14]2[CH:15]=[CH:16][C:11]([CH:7]3[O:6][CH2:10][CH2:9][O:8]3)=[CH:12][C:13]=2[O:22][CH3:23])[CH:21]=[CH:20][N:19]=1

Participants

7

Reactant 4

HCID 6214HexachloroethaneHCID 8028Tetrahydrofuran2×HCID 66961793HCID 66961793, compoundHCID 178418339Butyllithium

Product 1

HCID 66961006HCID 66961006, compoundYield 72.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a THF (50 mL) solution of 1-(4-[1,3]dioxolan-2-yl-2-methoxyphenyl)-1H-imidazole (3.85 g), n-butyllithium (1.6M hexane solution, 12 mL) was added dropwise under nitrogen atmosphere at −78° C., and the reaction solution was agitated for 30 minutes. THF (10 mL) solution of hexachloroethane (6.1 g) was added to the reaction solution and the reaction solution was agitated at room temperature for 1 hour after agitating for 30 minutes at −78° C. Water and ethyl acetate were added to the reaction mixture, and the organic layer was partitioned. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane-ethyl acetate system), and 3.19 g of the title compound was obtained. The physical properties of the compound are as follows.

Workup

  1. stirringthe reaction solution was agitated at room temperature for 1 hour
  2. stirringafter agitating for 30 minutes at −78° C
  3. customthe organic layer was partitioned
  4. washThe organic layer was washed with a saturated saline solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (elution solvent: hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-3f4a721eff3849ebaae9117a3c75759b
Source dataset
uspto-grants-2011_02
Patent number
US07880009B2

Reaction notes

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