Tetrahydrofuran → HCID 54411863, compound

HRID 2252278Notes

Reaction equation

HRID 2252278 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1.O1CCCC1.C([Li])CCC.Br[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>O.C(O)C>[CH2:22]([C:3]1[CH:4]=[CH:5][S:1][C:2]=1[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 81401-BromooctaneHCID 681202,2'-Bithiophene2×HCID 178418339Butyllithium

Product 1

HCID 54411863HCID 54411863, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The process is commenced by placing about 3 g of bithiophene in a round bottom flask with a side arm (for introducing an inert gas), followed by adding an anhydrous tetrahydrofuran to dissolve the bithiophene. The temperature of the solution is then lowered to −78° C. (using liquid nitrogen plus ethanol as coolant). Thereafter, about 5.8 ml of n-butyl lithium (n-BuLi) (2.5 M, dissolved in hexane) is gradually drop-added to the solution. After the temperature of the solution has returned to room temperature, the solution is continuously mixed for about 15 minutes. After this, 2.5 ml of 1-bromooctane (Br—C8H17) is added, and the solution is continuously stirred for about 10 hours. The reaction was carried out under the inert gas all the time. After a predetermined reaction time is reached, deionized water is added to terminate the reaction. An extraction is performed by adding ether to the solution. An organic layer is then collected. Another extraction of the organic layer is performed using a saturated sodium hydrogen carbonate aqueous solution, deionized water and a saturated sodium chloride solution, respectively. The resulting crude product is then purified using column chromatography (eluent is hexane) to obtain an intermediate product octylbithiophene (the yield is about 65.1%).

Workup

  1. additionfor introducing an inert gas),
  2. customis then lowered to −78° C.
  3. customhas returned to room temperature
  4. additionthe solution is continuously mixed for about 15 minutes
  5. additionis added
  6. customto terminate
  7. customthe reaction
  8. extractionAn extraction
  9. additionby adding ether to the solution
  10. customAn organic layer is then collected
  11. extractionAnother extraction of the organic layer
  12. customThe resulting crude product is then purified

Sources & evidence

ORD record
ord-91ad8e6863894d3ba9506a27bc961b2e
Source dataset
uspto-grants-2008_01
Patent number
US07321037B2

Reaction notes

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