Ethyl Acetate → 3-Pyridinol, 6-amino-2-(trifluoromethyl)-

HRID 1049343ノート

反応式

HRID 1049343 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]([NH2:19])=[N:13][C:14]=2[C:15]([F:18])([F:17])[F:16])O1.B(O[O-])=[O:22].O.[Na+].CCOC(C)=O>C1COCC1.O>[NH2:19][C:12]1[N:13]=[C:14]([C:15]([F:18])([F:17])[F:16])[C:9]([OH:22])=[CH:10][CH:11]=1

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 23695970Perboric acid, sodium salt, monohydrateHCID 904024785-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)pyridin-2-amine

生成物 1

HCID 904033283-Pyridinol, 6-amino-2-(trifluoromethyl)-収率 25%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)pyridin-2-amine (0.598 g, 2.076 mmol) in THF (10 mL) and water (10 mL) was treated with sodium perborate monohydrate (0.332 g, 3.32 mmol) and stirred at RT overnight. The mixture was treated with EtOAc and the solids removed via filtration through diatomaceous earth. The filtrate was treated with brine, extracted with EtOAc (3×) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford 6-amino-2-(trifluoromethyl)pyridin-3-ol (92 mg, 25%). 1H NMR (400 MHz, DMSO-d6): δ 9.47 (s, 1H), 7.15 (d, J=8.9 Hz, 1H), 6.58 (d, J=8.9 Hz, 1H), 5.70 (s, 2H); MS (ESI) m/z: 179.1 (M+H+).

後処理

  1. customthe solids removed via filtration through diatomaceous earth
  2. additionThe filtrate was treated with brine
  3. extractionextracted with EtOAc (3×)
  4. dry with materialthe combined organics were dried over Na2SO4
  5. concentrationconcentrated to dryness
  6. custompurified via silica gel chromatography (EtOAc/Hex)

出典と根拠

ORDレコード
ord-d78c7901059e48ef842d85d76c2c542d
出典データセット
uspto-grants-2016_07
特許番号
US09382228B2

反応ノート

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