Ethanol → Benzenebutanenitrile, .beta.-oxo-.alpha.-[3-(trifluoromethyl)phenyl]-
Reaction equation
[Na].C(O)C.[F:5][C:6]([F:17])([F:16])[C:7]1[CH:8]=[C:9]([CH2:13][C:14]#[N:15])[CH:10]=[CH:11][CH:12]=1.[C:18]1([CH2:24][C:25](OCC)=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[F:5][C:6]([F:16])([F:17])[C:7]1[CH:8]=[C:9]([CH:13]([C:25]([CH2:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:26])[C:14]#[N:15])[CH:10]=[CH:11][CH:12]=1Participants
Procedure
In this example, 4.91 g of metallic sodium was added to 110 ml of anhydrous ethanol at room temperature and stirred until all of the sodium dissolved. A mixture containing 18.76 g of (3-trifluoromethylphenyl)acetonitrile and 21.73 g of ethyl phenylacetate was then added dropwise and the resulting mixture was stirred at reflux for about 18 hours. The mixture was then poured into 300 ml water and extracted three times with ethyl ether. The pH of the extracted aqueous layer was adjusted to a pH of about 1 with aqueous 10 wt. % hydrochloric acid and again extracted three times with ethyl ether. The organic layer was washed twice with saturated aqueous sodium bicarbonate, dried over magnesium sulfate and evaporated to dryness under vacuum affording 22.6 g of the title compound.
Workup
- dissolutiondissolved
- additionwas then added dropwise
- temperatureat reflux for about 18 hours
- extractionextracted three times with ethyl ether
- extractionagain extracted three times with ethyl ether
- washThe organic layer was washed twice with saturated aqueous sodium bicarbonate
- dry with materialdried over magnesium sulfate
- customevaporated to dryness under vacuum
Sources & evidence
- ORD record
- ord-49605d1b4eb54723b0e3d3e2e958f459
- Source dataset
- uspto-grants-1986_02
- Patent number
- US04568376
Reaction notes
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