(2-Allyloxy-3-tert-butyl-5-methylphenyl)chlorodimethylsilane → (2-Allyloxy-3-tert-butyl-5-methylphenyl)(2,5-dimethylcyclopenta[1,2-b:4,3-b']dithiophen-7-yl)dimethylsilane

HRID 1295485Notes

Reaction equation

HRID 1295485 reaction equation
[CH2:1]([O:4][C:5]1[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:9][C:8]([CH3:15])=[CH:7][C:6]=1[Si:16](Cl)([CH3:18])[CH3:17])[CH:2]=[CH2:3].[CH3:20][CH:21]1[S:25][C:24]2=[C:26]([Li])[C:27]3[S:28][C:29]([CH3:32])=[CH:30][C:31]=3[C:23]2=[CH:22]1>C1(C)C=CC=CC=1.O1CCCC1>[CH2:1]([O:4][C:5]1[C:10]([C:11]([CH3:12])([CH3:13])[CH3:14])=[CH:9][C:8]([CH3:15])=[CH:7][C:6]=1[Si:16]([C:26]1[C:27]2[S:28][C:29]([CH3:32])=[CH:30][C:31]=2[C:23]2[C:24]=1[S:25][CH:21]([CH3:20])[CH:22]=2)([CH3:17])[CH3:18])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 21880918(2-Allyloxy-3-tert-butyl-5-methylphenyl)chlorodimethylsilaneHCID 178506637HCID 178506637, compound

Product 1

HCID 21881029(2-Allyloxy-3-tert-butyl-5-methylphenyl)(2,5-dimethylcyclopenta[1,2-b:4,3-b']dithiophen-7-yl)dimethylsilane

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2-allyloxy-3-tert-buyl-5-methylphenyl)chlorodimethylsilane (0.71 g, 2.40 mmol) in toluene (4 mL) was added dropwise to a solution of (2,5-dimethylcyclopenta[1,2-b:4,3-b′]dithiophen-7-yl)lithium (0.51 g, 2.40 mmol) in tetrahydrofuran (10 mL) at −78° C. The resulting reaction mixture was warmed to room temperature and stirred for 5 hours. After the solvent was distilled off under reduced pressure, hexane 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)(2,5-dimethylcyclopenta[1,2-b:4,3-b′]dithiophen-7-yl)dimethylsilane.

Workup

  1. customThe resulting reaction mixture
  2. distillationAfter the solvent was distilled off under reduced pressure, hexane
  3. additionwas added
  4. filtrationthe mixture was filtered
  5. customto remove insoluble substances
  6. concentrationThe filtrate was concentrated under reduced pressure to quantitatively obtain (2-allyloxy-3-tert-butyl-5-methylphenyl)(2,5-dimethylcyclopenta[1,2-b:4,3-b′]dithiophen-7-yl)dimethylsilane

Sources & evidence

ORD record
ord-6b1efef458d047da8641283417d3dd67
Source dataset
uspto-grants-2007_07
Patent number
US07241927B2

Reaction notes

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