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

HRID 1295489Notes

Reaction equation

HRID 1295489 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-3515dda57e50450d8f34a8605e9ec26c
Source dataset
uspto-grants-2007_07
Patent number
US07241927B2

Reaction notes

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