Trifluoroacetic acid → HCID 66618946, compound

HRID 406370Notes

Reaction equation

HRID 406370 reaction equation
[C:1]([CH2:3][CH2:4][CH:5]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]([F:22])([F:21])[F:20])[C:6]([O:8]C(C)(C)C)=[O:7])#[N:2].FC(F)(F)C(O)=O>C(Cl)Cl.C(OCC)C>[C:1]([CH2:3][CH2:4][CH:5]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]([F:20])([F:22])[F:21])[C:6]([OH:8])=[O:7])#[N:2]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66618877HCID 66618877, compound

Product 1

HCID 66618946HCID 66618946, compoundYield 114.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-cyano-2-(2-trifluoromethylphenyl)butanoate (7.2 g) was dissolved in methylene chloride (40 mL). Trifluoroacetic acid (50 mL) was added at 0° C. and the reaction was initiated. After stirring at room temperature for one hour, concentration under reduced pressure gave an oil. The resulting oil was dissolved in diethyl ether, washed with water (three times) and brine and dried over magnesium sulfate. Concentration under reduced pressure gave a yellow oil. The oil was dissolved again in diethyl ether and partitioned between diethyl ether and 5 N sodium hydroxide (15 mL). The resulting aqueous layer was made acidic with 5 N hydrochloric acid (16 mL) and extracted with methylene chloride twice to obtain the title compound (6.76 g) as a colorless transparent oil.

Workup

  1. concentrationconcentration under reduced pressure
  2. customgave an oil
  3. washwashed with water (three times) and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationConcentration under reduced pressure
  6. customgave a yellow oil
  7. custompartitioned between diethyl ether and 5 N sodium hydroxide (15 mL)
  8. extractionextracted with methylene chloride twice

Sources & evidence

ORD record
ord-bd7553a183964d958459cf8281aae9d3
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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