Reacción #582498

Ecuación de reacción

Sodium acetylide

p-methoxyphenyl-thiophene-2-yl-ketone

DMSO

→

1-(4methoxyphenyl)-1-(thiophene-2-yl)prop-2-yn-1-ol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   Otrowhile bubbling acetylene gas
3. 3
   workup.ADDITIONAfter addition
4. 4
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 2 hours
5. 5
   workup.ADDITIONpoured
6. 6
   Otroonto crushed ice
7. 7
   ExtracciónAfter extraction with methylene chloride (20 ml
8. 8
   Secado2×10 ml), the mixture was dried over anhydrous sodium sulfate
9. 9
   Filtraciónfiltered
10. 10
    OtroEvaporation of the solvent
11. 11
    Otrogave an oil that
12. 12
    Otrowas purified
13. 13
    Otroby flush chromatography on neutral alumina (activity III)
14. 14
    OtroDe-coloration with a small amount of charcoal followed by removal of solvent

Procedimiento

Sodium acetylide (1.37 g, 33.5 mmol) suspended in dry DMSO (25 ml) was added to p-methoxyphenyl-thiophene-2-yl-ketone (4.8 g, 22 mmol) in portions with stirring under water bath cooling while bubbling acetylene gas. After addition, the reaction mixture was stirred at room temperature for 2 hours, poured onto crushed ice, acidified with 4 M hydrochloric acid until the pH was approximately 6. After extraction with methylene chloride (20 ml, then 2×10 ml), the mixture was dried over anhydrous sodium sulfate and filtered. Evaporation of the solvent gave an oil that was purified by flush chromatography on neutral alumina (activity III) using hexane/methylene chloride (2:1) as eluent. De-coloration with a small amount of charcoal followed by removal of solvent afforded the relatively clean 1-(4methoxyphenyl)-1-(thiophene-2-yl)prop-2-yn-1-ol as yellow-brown oil.

Fuente