反应详情

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-(4-methoxyphenyl)-1-(thiophene-2-yl)prop-2-yn-1-ol as yellow-brown oil.

1. temperaturecooling
2. customwhile bubbling acetylene gas
3. additionAfter addition
4. stirringthe reaction mixture was stirred at room temperature for 2 hours
5. additionpoured
6. customonto crushed ice
7. extractionAfter extraction with methylene chloride (20 ml
8. dry with material2×10 ml), the mixture was dried over anhydrous sodium sulfate
9. filtrationfiltered
10. customEvaporation of the solvent
11. customgave an oil that
12. customwas purified
13. customby flush chromatography on neutral alumina (activity III)
14. customDe-coloration with a small amount of charcoal followed by removal of solvent