Potassium Hydroxide → 9H-Fluorene, 2,7-diethynyl-

HRID 1840693Notes

Reaction equation

HRID 1840693 reaction equation
[OH-].[K+].C[Si]([C:7]#[C:8][C:9]1[CH:21]=[CH:20][C:19]2[C:18]3[C:13](=[CH:14][C:15]([C:22]#[C:23][Si](C)(C)C)=[CH:16][CH:17]=3)[CH2:12][C:11]=2[CH:10]=1)(C)C>CO>[C:22]([C:15]1[CH:16]=[CH:17][C:18]2[C:19]3[C:11](=[CH:10][C:9]([C:8]#[CH:7])=[CH:21][CH:20]=3)[CH2:12][C:13]=2[CH:14]=1)#[CH:23]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 15393909HCID 15393909, compound

Product 1

HCID 121072229H-Fluorene, 2,7-diethynyl-Yield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Thereafter, 60 ml of 1N potassium hydroxide solution was slowly added to 10.12 g(28.2 mmol) of 2,7-di(trimethylsilylethynyl)fluorene dissolved in 150 mL of methanol. The reaction mixture was stirred for 3 h at room temperature and solvent was removed. Residue was extracted with ether and the ether layer was washed with distilled water. The washed ether layer was concentrated. The crude product was purified by column chromatography on silica gel by eluting with hexane/ethylacetate (15/1) to give 1.35 g (72%) of 2,7-diethynylfluorene of which mp was 125° C.

Workup

  1. customsolvent was removed
  2. extractionResidue was extracted with ether
  3. washthe ether layer was washed with distilled water
  4. concentrationThe washed ether layer was concentrated
  5. customThe crude product was purified by column chromatography on silica gel
  6. washby eluting with hexane/ethylacetate (15/1)

Sources & evidence

ORD record
ord-eda9f19b28324c419d504e2777b69c56
Source dataset
uspto-grants-2004_01
Patent number
US06682782B2

Reaction notes

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