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

HRID 1910066ノート

反応式

HRID 1910066 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-a7c2bf9b42e04b6d811949178044671f
出典データセット
uspto-grants-2013_12
特許番号
US08598156B2

反応ノート

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