Water → 2-Dodecylthiophene

HRID 2093122Notes

Reaction equation

HRID 2093122 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.C([Li])CCC.[CH2:11](Br)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].O>O1CCCC1.ClCCl>[CH2:22]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH3:11]

Participants

7

Reactant 4

HCID 962WaterHCID 8030ThiopheneHCID 89191-BromododecaneHCID 178418339Butyllithium

Product 1

HCID 5663472-DodecylthiopheneYield 54.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

8.0 g of thiophene was dissolved in 150 ml of tetrahydrofuran and cooled to 0° C. To this solution, 62 ml of n-butyllithium solution (1.6 mol/l hexane solution) was added dropwise, and stirred for 3 hours. 25.0 g of n-dodecylbromide was added dropwise to the solution, and was stirred at room temperature for 18 hours. 150 ml of water and 150 ml of dichloromethane were added to the resulting solution to separate the organic layer. The organic layer was washed with 300 ml of water and dried over anhydrous magnesium sulfate. The solvent was distilled off from the resulting solution under reduced pressure with a rotary evaporator and then the solution was distilled under reduced pressure to obtain 13 g of 2-n-dodecylthiophene.

Workup

  1. stirringwas stirred at room temperature for 18 hours
  2. customto separate the organic layer
  3. washThe organic layer was washed with 300 ml of water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off from the resulting solution under reduced pressure with a rotary evaporator
  6. distillationthe solution was distilled under reduced pressure

Sources & evidence

ORD record
ord-73daaf730d294c04866af59ce5f0e935
Source dataset
uspto-grants-2013_05
Patent number
US08441002B2

Reaction notes

Loading…