Dimethyl Sulfoxide → HCID 15832587, compound

HRID 352650

Reaction equation

HRID 352650 reaction equation
[C-]#[C-].[Na+].[Na+].COC1C=CC([C:13]2C=CS[C:14]=2[C:18]([C:20]2[S:21][CH:22]=[CH:23][C:24]=2[C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=O)=CC=1.CS(C)=[O:35]>>[CH3:32][O:31][C:28]1[CH:27]=[CH:26][C:25]([C:24]([C:20]2[S:21][CH:13]=[CH:14][CH:18]=2)([OH:35])[C:23]#[CH:22])=[CH:30][CH:29]=1

Participants

4

Reactant 3

HCID 679Dimethyl SulfoxideHCID 68533024HCID 68533024, compoundHCID 178463197HCID 178463197, compound

Product 1

HCID 15832587HCID 15832587, compound

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-05df742b0c0d4daa886aff4a5ca811b2
Source dataset
uspto-grants-2004_06
Patent number
US06747145B2

Linked notes

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