Water → 2-Hexadecylthiophene
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][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].O>O1CCCC1.ClCCl>[CH2:26]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH3:11]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
7.2 g of thiophene was dissolved in 100 ml of tetrahydrofuran and cooled to 0° C. To this solution, 56 ml of n-butyllithium solution (1.6 mol/l hexane solution) was added dropwise and stirred for 3.5 hours. To this solution, 25 g of hexadecylbromide was added dropwise and stirred at room temperature for 5.5 hours. 100 ml of water and 100 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 resulting solution was concentrated by a rotary evaporator and purified by a column chromatography (filler: silica gel, eluent: hexane) to obtain 4.4 g of 2-n-hexadecylthiophene represented by the following formula.
Workup
- stirringstirred at room temperature for 5.5 hours
- customto separate the organic layer
- washThe organic layer was washed with 300 ml of water
- dry with materialdried over anhydrous magnesium sulfate
- concentrationThe resulting solution was concentrated by a rotary evaporator
- custompurified by a column chromatography (filler: silica gel, eluent: hexane)
Sources & evidence
- ORD record
- ord-2e8d2a7113f84c6da2e0cfdac07aa243
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08441002B2
Reaction notes
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