Trifluoroacetic acid → 2-(6-(Trifluoromethyl)pyridin-2-yl)acetic acid

HRID 1910066Notes

Reaction equation

HRID 1910066 reaction equation
CC([CH:5]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[N:10]=1)[C:6]([O-:8])=[O:7])(C)C.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>ClCCl>[F:17][C:15]([F:16])([F:18])[C:11]1[N:10]=[C:9]([CH2:5][C:6]([OH:8])=[O:7])[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 867621751,1-Dimethylethyl[6-(trifluoromethyl)-2-pyridinyl]acetate

Product 1

HCID 534015132-(6-(Trifluoromethyl)pyridin-2-yl)acetic acidYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl[6-(trifluoromethyl)-2-pyridinyl]acetate (698 mg, 2.67 mmol), triethylsilane (1.067 mL, 6.68 mmol) in Dichloromethane (DCM) (10 mL) was added TFA (2.68 mL, 34.7 mmol) dropwise via syringe. The reaction was stirred overnight at room temperature. LCMS analysis indicated good conversion, so the reaction was concentrated to a yellow oil. 5 mL of diethyl ether was added but no precipitation occurred, so the solution was concentrated to afford [6-(trifluoromethyl)-2-pyridinyl]acetic acid (535 mg, 2.61 mmol, 98% yield) as a yellow oil which solidified to a yellow solid. LC-MS (ES) m/z=206 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.89 (s, 2H), 7.70 (d, J=7.83 Hz, 1H), 7.81 (d, J=7.58 Hz, 1H), 7.97-8.16 (m, 1H), 12.26-12.88 (br. s., 1H).

Workup

  1. concentrationso the reaction was concentrated to a yellow oil
  2. addition5 mL of diethyl ether was added
  3. customno precipitation
  4. concentrationwas concentrated

Sources & evidence

ORD record
ord-a7c2bf9b42e04b6d811949178044671f
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

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