Water → 4-(2-Trifluoromethylphenyl)-3-buten-2-one
Reaction equation
CON(C)[C:4](=[O:17])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]([F:16])([F:15])[F:14].C[Li].O.[C:22](OCC)(=O)C>O1CCCC1.C(OCC)C>[F:14][C:13]([F:16])([F:15])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH:6]=[CH:5][C:4](=[O:17])[CH3:22]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
11 g of N-methoxy-N-methyl-3-(2-trifluoromethylphenyl)acrylamide are dissolved in 150 ml of dry tetrahydrofuran under a nitrogen atmosphere, cooled to −78° C. and treated dropwise with 36 ml of a 1.4N solution of methyllithium in diethyl ether in 10 minutes. The solution is subsequently furthermore stirred at −78° C. for 2 h and then hydrolysed with water. 200 ml of ethyl acetate are now added at ambient temperature and the mixture is washed three times with saturated sodium chloride solution. The organic phase is finally separated, dried with magnesium sulfate and evaporated under reduced pressure. After purifying by flash chromatography, the title compound is thus obtained.
Workup
- washthe mixture is washed three times with saturated sodium chloride solution
- customThe organic phase is finally separated
- dry with materialdried with magnesium sulfate
- customevaporated under reduced pressure
- customAfter purifying by flash chromatography
Sources & evidence
- ORD record
- ord-b59c10a751ce41438cf1eb1cd9957f87
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07091371B2
Reaction notes
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