Tetrahydrofuran → (2-Allyloxy-3-tert-butyl-5-methylphenyl)(cyclopenta[1,2-b:4,3-b']dithiophen-7-yl)diethylsilane

HRID 724500Notes

Reaction equation

HRID 724500 reaction equation
[S:1]1[CH2:5][CH:4]=[C:3]2[C:6]3[CH:10]=[CH:9][S:8][C:7]=3C=[C:2]12.[CH2:12]([Li])[CH2:13]CC.[CH2:17]([O:20][C:21]1[C:26]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:25][C:24]([CH3:31])=[CH:23][C:22]=1[Si:32](Cl)([CH3:34])[CH3:33])[CH:18]=[CH2:19].O1CCC[CH2:37]1>C1(C)C=CC=CC=1>[CH2:17]([O:20][C:21]1[C:26]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:25][C:24]([CH3:31])=[CH:23][C:22]=1[Si:32]([C:34]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[C:3]2[C:2]=1[S:1][CH2:5][CH:4]=2)([CH2:12][CH3:13])[CH2:33][CH3:37])[CH:18]=[CH2:19]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 21880918(2-Allyloxy-3-tert-butyl-5-methylphenyl)chlorodimethylsilaneHCID 21881014Cyclopenta[1,2-b:4,3-b']dithiopheneHCID 178418339Butyllithium

Product 1

HCID 21881049(2-Allyloxy-3-tert-butyl-5-methylphenyl)(cyclopenta[1,2-b:4,3-b']dithiophen-7-yl)diethylsilane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of cyclopenta[1,2-b:4,3-b′]dithiophene (0.50 g, 280 mmol) in tetrahydrofuran (25 mL) was added dropwise n-butyllithium (1.56 M, 1.88 mL, 2.94 mmol) at −78° C. and stirred at room temperature for 4 hours. The mixture was cooled to −78° C. and a solution of (2-allyloxy-3-tert-buyl-5-methylphenyl)chlorodimethylsilane (0.83 g, 2.80 mmol) in toluene (5 mL) was added dropwise thereto. The resulting reaction mixture was warmed to room temperature and stirred for 2 hours. After the solvent was distilled off under reduced pressure, toluene was added and the mixture was filtered to remove insoluble substances. The filtrate was concentrated under reduced pressure to quantitatively obtain (2-allyloxy-3-tert-butyl-5-methylphenyl)(cyclopenta[1,2-b:4,3-b′]dithiophen-7-yl)diethylsilane.

Workup

  1. temperatureThe mixture was cooled to −78° C.
  2. customThe resulting reaction mixture
  3. temperaturewas warmed to room temperature
  4. stirringstirred for 2 hours
  5. distillationAfter the solvent was distilled off under reduced pressure, toluene
  6. additionwas added
  7. filtrationthe mixture was filtered
  8. customto remove insoluble substances
  9. concentrationThe filtrate was concentrated under reduced pressure to quantitatively obtain (2-allyloxy-3-tert-butyl-5-methylphenyl)(cyclopenta[1,2-b:4,3-b′]dithiophen-7-yl)diethylsilane

Sources & evidence

ORD record
ord-9916452a3b7e489e904b9108c27f1bdc
Source dataset
uspto-grants-2006_11
Patent number
US07141690B2

Reaction notes

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