Diethyl Ether → HCID 15896190, compound

HRID 991936Notes

Reaction equation

HRID 991936 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]2[CH3:14])[N:3]=1.C([Li])CCC.CCCCCC.CCOCC.I[C:32]1[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][Cl:40])=[CH:34][CH:33]=1>[Cl-].[Zn+2].[Cl-].O1CCCC1>[CH3:14][C:9]1[N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([C:32]3[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][Cl:40])=[CH:34][CH:33]=3)[N:3]=2)[C:12]([CH3:13])=[CH:11][CH:10]=1

Participants

8

Reactant 5

HCID 3283Diethyl EtherHCID 8058HexaneHCID 155127672-Bromo-6-(2,5-dimethyl-1H-pyrrol-1-yl)pyridineHCID 15896189HCID 15896189, compoundHCID 178418339Butyllithium

Product 1

HCID 15896190HCID 15896190, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a 1 L 3-neck round-bottomed flask equipped with addition funnel and nitrogen inlet were added 10.0 g (40 mmol) 2-bromo-6-(2, 5-dimethylpyrrol-1-yl)pyridine and 200 mL dry tetrahydrofuran. The solution was cooled at −78° C., and a 1.6 M solution of butyl lithium in hexane (25 mL, 40 mmol) was added dropwise over 10 min. The reaction was stirred at −78° C. for 20 min, then a 1.0 M solution of zinc chloride in ether (100 mL, 100 mmol) was added dropwise over 40 min keeping the temperature at −70° C. The reaction was then allowed to warm to room temperature, and 11.0 g (40 mmol) 2-(4-iodophenyl)ethylchloride was added, followed by 200 mg tetrakistriphenylphosphine palladium. The reaction was refluxed for 3 hours, cooled, and filtered through Celite. The filtrate was evaporated, and the residue taken up in ethyl acetate, washed with brine, dried over sodium sulfate, and evaporated. The residue was filtered through silica gel with methylene chloride, concentrated, and chromatographed on silica gel using 1% ethyl acetate in hexane as eluant to afford 7.3 g (59%) of the product as an oil.

Workup

  1. customTo a 1 L 3-neck round-bottomed flask equipped with addition funnel and nitrogen inlet
  2. customat −70° C
  3. temperatureto warm to room temperature
  4. temperatureThe reaction was refluxed for 3 hours
  5. temperaturecooled
  6. filtrationfiltered through Celite
  7. customThe filtrate was evaporated
  8. washwashed with brine
  9. dry with materialdried over sodium sulfate
  10. customevaporated
  11. filtrationThe residue was filtered through silica gel with methylene chloride
  12. concentrationconcentrated
  13. customchromatographed on silica gel using 1% ethyl acetate in hexane as eluant

Sources & evidence

ORD record
ord-5552a685bb304c4f8378bc97b8c9f473
Source dataset
uspto-grants-2002_10
Patent number
US06465491B2

Reaction notes

Loading…