Potassium Carbonate → 2-Ethynyl-9,9-dioctyl-9H-fluorene

HRID 458494Notes

Reaction equation

HRID 458494 reaction equation
[CH2:1]([C:9]1([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:21]2[CH:20]=[C:19]([C:22]#[C:23][Si](C)(C)C)[CH:18]=[CH:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:22]([C:19]1[CH:18]=[CH:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:21]=2[CH:20]=1)#[CH:23]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 18442167(9,9-Dioctyl-9H-fluoren-2-ylethynyl)-trimethylsilane

Product 1

HCID 184421662-Ethynyl-9,9-dioctyl-9H-fluoreneYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (9,9-dioctyl-9H-fluoren-2-ylethynyl)-trimethylsilane (10.3 g, 21.2 mmol) in ethanol was added potassium carbonate (2.92 g, 21.2 mmol). The mixture was stirred at room temperature for 20 hours and then filtered. The filtrate was evaporated to dryness and the residue taken up in hexane. Washing with water, drying over magnesium sulfate and evaporation gave an oil characterized as 2-ethynyl-9,9-dioctyl-9H-fluorene (7.20 g, 82% yield).

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated to dryness
  3. washWashing with water
  4. dry with materialdrying over magnesium sulfate and evaporation
  5. customgave an oil

Sources & evidence

ORD record
ord-84c392785ba34defb89abb73f69cf9b1
Source dataset
uspto-grants-2007_03
Patent number
US07192657B2

Reaction notes

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