Acetone → 2-Ethynyl-5-(4-pyridyl)ethynyl Thiophene

HRID 234044

Reaktionsgleichung

Reaktionsgleichung von HRID 234044
CC(O)(C)[C:3]#[C:4][C:5]1[S:6][C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[CH:8][CH:9]=1.[OH-].[K+].CC(C)=O.C1COCC1.CCCCCC>CO.C1(C)C=CC=CC=1>[C:4]([C:5]1[S:6][C:7]([C:10]#[C:11][C:12]2[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=2)=[CH:8][CH:9]=1)#[CH:3]

Komponenten

7

Edukt 4

HCID 180AcetoneHCID 14797Potassium HydroxideHCID 21883165Tetrahydrofuran hexaneHCID 233581552-{3-Methyl-3-hydroxybutynyl}-5-{2-(4-pyridyl)ethynyl}thiophene

Produkt 1

HCID 153942682-Ethynyl-5-(4-pyridyl)ethynyl ThiopheneAusbeute 69,92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A distillation apparatus was set up and 2-{3-methyl-3-hydroxybutynyl}-5-{2-(4pyridyl)ethynyl}thiophene (8.50 g, 31.84 mmol), KOH (1.78 g, 21.84 mmol) in 25 ml of methanol and 200 ml of toluene were added to the distillation flask. The flask was heated to about 90° C. until all the acetone formed in the reaction and the methanol were collected in the receiving flask (total heating time, about 1.5 to 2 hours). The toluene was removed under reduced pressure and the reddish residue was purified by chromatography on silica gel using 2:8 THF/petroleum ether as the eluting solvent to obtain 4.65 g (69.92% yield) of light yellow solid. TLC (3:7 THF/hexane): Rf =0.28, mp=134.5°-135.5° C. FTIR (cm-1): 3304 (H--C≡C), 2206 (C≡C). Elemental analysis: Calculated for C13H7NS (mw 209.26): C, 74.61; H, 3.37; N, 6.70. Found: C, 74.54; H, 3.19; N, 6.72. DSC thermogram of the monomer showed a melting transition at 138° C. and a transition for thermal curing of the terminal C≡C at 144.67° C. TGA thermogram showed about 10-20% weight loss at the terminal C≡C cure temperature (about 150° C.) after which there was little weight loss up to about 400° C.

Aufarbeitung

  1. customformed in the reaction
  2. customthe methanol were collected in the receiving flask (total heating time, about 1.5 to 2 hours)
  3. customThe toluene was removed under reduced pressure
  4. customthe reddish residue was purified by chromatography on silica gel using 2:8 THF/petroleum ether as the eluting solvent
  5. customto obtain 4.65 g (69.92% yield) of light yellow solid
  6. customat 138° C.
  7. customat 144.67° C
  8. customup to about 400° C.

Quellen und Nachweise

ORD-Eintrag
ord-791635f4d1cd40ad8b9daa3b62e6dd00
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05594075

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