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[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]=1참가 물질
실험 절차
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.
후처리
- temperaturecooling
- customwhile bubbling acetylene gas
- additionAfter addition
- stirringthe reaction mixture was stirred at room temperature for 2 hours
- additionpoured
- customonto crushed ice
- extractionAfter extraction with methylene chloride (20 ml
- dry with material2×10 ml), the mixture was dried over anhydrous sodium sulfate
- filtrationfiltered
- customEvaporation of the solvent
- customgave an oil that
- customwas purified
- customby flush chromatography on neutral alumina (activity III)
- customDe-coloration with a small amount of charcoal followed by removal of solvent
출처 및 근거
- ORD 기록
- ord-05df742b0c0d4daa886aff4a5ca811b2
- 출처 데이터셋
- uspto-grants-2004_06
- 특허 번호
- US06747145B2
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