Thiophene → HCID 178418439, compound

HRID 2372677Notes

Reaction equation

HRID 2372677 reaction equation
S1C=C[CH:3]=[CH:2]1.[CH2:6]([Li:10])[CH2:7][CH2:8][CH3:9].[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[Li:16]>C1COCC1>[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[Li:16].[C:6]1([Li:10])[CH:3]=[CH:2][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 8030ThiopheneHCID 178418339Butyllithium2×HCID 178418439HCID 178418439, compound

Product 2

HCID 178418439HCID 178418439, compoundHCID 178506676HCID 178506676, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

Methyllithium in THF/toluene, methyllithium in THF/cumene with magnesium, dimethyl magnesium in THF/toluene and THF/cumene, ethyllithium in THF/cyclohexane, pure ethyllithium solid, butyllithium in hexane, concentrated butyllithium in hexane, and phenyllithium in cyclohexane were obtained from Lithium Corporation of America (Lithco). Thienyllithium was prepared from thiophene, butyllithium in hexanes and THF, by the following method: 1 mole of thienyllithium and 1.2 mole of THF were mixed in a dry, argon purged round bottom three neck flask. The solution was stirred, cooled to -20° C. and then 0.95 mole butyllithium (17-25 wt % in hexane) was added drop wise over 45 minutes to 1 hour. The reaction temperature was maintained at -20° C. for 2-3 hours, then allowed to warm to room temperature overnight. The reaction mixture was stirred constantly during the reaction. The product, a 1:1 complex of thienyllithium and THF was filtered and stored in a glass bottle equipped with a ground glass joint. Solid phenyllithium was prepared by concentration of Lithco's phenyllithium product in hexanes, and collection of the solid by filtration. An argon atmosphere was maintained over all organolithium solids and solution during all procedures. All glassware was thoroughly cleaned, baked at 150° C. overnight, then purged cool with argon before use.

Workup

  1. temperatureThe reaction temperature was maintained at -20° C. for 2-3 hours
  2. temperatureto warm to room temperature overnight
  3. stirringThe reaction mixture was stirred constantly during the reaction
  4. filtrationThe product, a 1:1 complex of thienyllithium and THF was filtered
  5. customequipped with a ground glass joint
  6. custompurged
  7. temperaturecool with argon before use

Sources & evidence

ORD record
ord-040bea81fee6487bbe6a8fdf3b65f7c7
Source dataset
uspto-grants-1992_03
Patent number
US05100575

Reaction notes

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