Hexachloroethane → HCID 59574160, compound

HRID 2092048Notes

Reaction equation

HRID 2092048 reaction equation
O1CCCC1.[Si:6]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([F:21])[CH:16]=1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].C([N-]C(C)C)(C)C.[Li+].[Cl:30]C(Cl)(Cl)C(Cl)(Cl)Cl>C(OCC)(=O)C>[Si:6]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([F:21])[C:16]=1[Cl:30])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 6214HexachloroethaneHCID 8028TetrahydrofuranHCID 2724682Lithium diisopropylamideHCID 59574609HCID 59574609, compound

Product 1

HCID 59574160HCID 59574160, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A tetrahydrofuran solution (10 mL) of 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-fluoropyridine (469.1 mg, 1.94 mmol) was mixed with lithium diisopropylamide (1.08 M in tetrahydrofuran, 2.16 mL, 2.33 mmol) under cooling with ice. The reaction mixture was stirred at 0° C. for an hour, then added to hexachloroethane (840.0 mg, 3.50 mmol) and warmed slowly to room temperature for 12 hours with stirring. After completion of the reaction, the reaction solution was mixed with ethyl acetate, and the organic layer was washed with saturated aqueous ammonium chloride, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1 to 5/1) to give the desired product (157.7 mg, 30% yield).

Workup

  1. temperatureunder cooling with ice
  2. temperaturewarmed slowly to room temperature for 12 hours
  3. stirringwith stirring
  4. customAfter completion of the reaction
  5. washthe organic layer was washed with saturated aqueous ammonium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1 to 5/1)

Sources & evidence

ORD record
ord-8f9c0faac75549db9b284d5a487aeee6
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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