반응 #217835

반응 방정식

3,5-bis(phenylethynyl)benzil

1,3-diphenylacetone

1-propanol

benzyltrimethylammonium hydroxide

→

4-(3,5-bis(phenylethynyl)phenyl)-2,3,5-triphenylcyclopentadienone

수율 76.4%

용매

toluene

반응 조건

후처리

1. 1
   workup.ADDITIONcontaining a predried magnetic stirring bar
2. 2
   온도cooled spiral condenser
3. 3
   온도a thermometer with thermostatically controlled heating mantle
4. 4
   온도heating commenced
5. 5
   기타once a refluxing clear light yellow colored solution formed
6. 6
   온도After maintaining the
7. 7
   온도reflux for 20 reactant
8. 8
   기타After a cumulative 30 minutes of reaction
9. 9
   기타the heating mantle was removed from the reactor
10. 10
    여과The product was recovered via filtration through a medium
11. 11
    기타fitted glass funnel
12. 12
    세척The product cake on the funnel was washed with two portions (50 milliliters) of 1-propanol
13. 13
    기타dried in a vacuum oven

실험 절차

A portion of the 3,5-bis(phenylethynyl)benzil (10.87 grams, 0.0265 mole), 1,3-diphenylacetone (5.90 grams, 0.0281 mole), anhydrous 1-propanol (300 milliliters) and anhydrous toluene (17 milliliters), both of which had been sparged with dry nitrogen, were added under a dry nitrogen atmosphere to a predried 500 milliliter glass three neck round bottom reactor containing a predried magnetic stirring bar. The reactor was additionally outfitted with a fan cooled spiral condenser and a thermometer with thermostatically controlled heating mantle. Stirring and heating commenced, and once a refluxing clear light yellow colored solution formed, benzyltrimethylammonium hydroxide (40 percent in methanol) (0.91 gram) was added, immediately inducing a dark red color. After maintaining the reflux for 20 reactant had been achieved. After a cumulative 30 minutes of reaction, the heating mantle was removed from the reactor, and the stirred contents were maintained at 24° C. for the next 16 hours. The product was recovered via filtration through a medium fitted glass funnel. The product cake on the funnel was washed with two portions (50 milliliters) of 1-propanol, then dried in a vacuum oven to provide 11.84 grams (76.4 percent isolated yield) of 4-(3,5-bis(phenylethynyl)phenyl)-2,3,5-triphenylcyclopentadienone (unsymmetrically substituted 3,5-AAB monomer) as a dark red purple colored crystalline product. HPLC analysis revealed the presence of the desired product at 100 area percent. The product's identity was confirmed by 1H NMR and El MS analysis.

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