(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 724496Notes

Reaction equation

HRID 724496 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-7a31c02452d54a248d81d824062fc843
Source dataset
uspto-grants-2006_11
Patent number
US07141690B2

Reaction notes

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