HCID 21880924, compound → HCID 21880978, compound

HRID 724497Notes

Reaction equation

HRID 724497 reaction equation
C([Li])CCC.[CH3:6][CH:7]1[S:11][C:10]2=[CH:12][C:13]3[S:14][C:15]([CH3:18])=[CH:16][C:17]=3[C:9]2=[CH:8]1.[CH2:19]([O:22][C:23]1[C:28]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:27][C:26]([CH3:33])=[CH:25][C:24]=1[Si:34](Cl)([CH2:37][CH3:38])[CH2:35][CH3:36])[CH:20]=[CH2:21]>O1CCCC1.C1(C)C=CC=CC=1>[CH2:19]([O:22][C:23]1[C:28]([C:29]([CH3:30])([CH3:31])[CH3:32])=[CH:27][C:26]([CH3:33])=[CH:25][C:24]=1[Si:34]([C:12]1[C:13]2[S:14][C:15]([CH3:18])=[CH:16][C:17]=2[C:9]2[C:10]=1[S:11][CH:7]([CH3:6])[CH:8]=2)([CH2:35][CH3:36])[CH2:37][CH3:38])[CH:20]=[CH2:21]

Participants

6

Reactant 3

HCID 21880924HCID 21880924, compoundHCID 67206735(2-Allyloxy-3-tert-butyl-5-methylphenyl)chlorodiethylsilaneHCID 178418339Butyllithium

Product 1

HCID 21880978HCID 21880978, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

At −78° C., n-butyllithium (1.56 M, 1.69 mL, 2.64 mmol) was added dropwise to a solution of 2,5-dimethylcyclopenta[1,2-b:4,3-b′]dithiophen (0.50 g, 2.42 mmol) in tetrahydrofuran (10 mL) and the mixture was stirred at room temperature for 4 hours. After the reaction mixture was cooled to −78° C., a solution of (2-allyloxy-3-tert-buyl-5-methylphenyl)chlorodiethylsilane (0.72 g, 2.20 mmol) in toluene (3 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)(2,5-dimethylcyclopenta[1,2-b:4,3-b′]dithiophen-7-yl)diethylsilane.

Workup

  1. temperatureAfter the reaction 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)(2,5-dimethylcyclopenta[1,2-b:4,3-b′]dithiophen-7-yl)diethylsilane

Sources & evidence

ORD record
ord-eb56857b284943b4b1889f27cb0c9984
Source dataset
uspto-grants-2006_11
Patent number
US07141690B2

Reaction notes

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