Methyl Acrylate → Methyl 4-cyano-4-(2-trifluoromethylphenyl)butanoate

HRID 406361Notes

Reaction equation

HRID 406361 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]#[N:11].C1OCCOCCOCCOCCOCCOC1.[C:32]([O:36][CH3:37])(=[O:35])[CH:33]=[CH2:34]>O1CCCC1.CC(C)([O-])C.[K+]>[C:10]([CH:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:2]([F:12])([F:13])[F:1])[CH2:34][CH2:33][C:32]([O:36][CH3:37])=[O:35])#[N:11]

Participants

6

Reactant 3

HCID 7294Methyl AcrylateHCID 2855718-Crown-6HCID 764352-(Trifluoromethyl)phenylacetonitrile

Product 1

HCID 66618793Methyl 4-cyano-4-(2-trifluoromethylphenyl)butanoate

Reagents, catalysts & solvents 2

HCID 23665647Potassium tert-butoxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-(Trifluoromethyl)phenylacetonitrile (2.0 g) was dissolved in tetrahydrofuran (50 mL). Potassium tert-butoxide (60.6 mg), 18-crown-6 (2.85 g) and methyl acrylate (973 μL) were added at 0° C. and the mixture was stirred at the same temperature for 40 minutes. The reaction was terminated with saturated ammonium chloride, followed by dilution with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. Concentration under reduced pressure gave an oil. The oil was purified by silica gel column chromatography (mobile phase:ethyl acetate/heptane=0 to 30%) to obtain the title compound (2.2 g).

Workup

  1. customThe reaction was terminated with saturated ammonium chloride
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationConcentration under reduced pressure
  5. customgave an oil
  6. customThe oil was purified by silica gel column chromatography (mobile phase:ethyl acetate/heptane=0 to 30%)

Sources & evidence

ORD record
ord-af00e3dc846f42daacbf0b123124741a
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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