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Water → 4-(2-Trifluoromethylphenyl)-3-buten-2-one

HRID 9927
Notes
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Reaction equation

HRID 9927 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 73858026N-methoxy-N-methyl-3-(2-trifluoromethylphenyl)acrylamideHCID 178418348HCID 178418348, compound

Product 1

HCID 5226124-(2-Trifluoromethylphenyl)-3-buten-2-one

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
HCID 8028TetrahydrofuranSolvent

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

  1. washthe mixture is washed three times with saturated sodium chloride solution
  2. customThe organic phase is finally separated
  3. dry with materialdried with magnesium sulfate
  4. customevaporated under reduced pressure
  5. customAfter purifying by flash chromatography

Sources & evidence

ORD record
ord-b59c10a751ce41438cf1eb1cd9957f87
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07091371B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes