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

HRID 1910066노트

반응식

HRID 1910066 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-a7c2bf9b42e04b6d811949178044671f
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598156B2

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