Ethyl 3-oxo-3-(pyridin-2-yl)propanoate → HCID 178472895、化合物

HRID 714928

反応式

HRID 714928 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:8].[N:15]([O-])=[O:16].[Na+]>C(O)(=O)C.O>[OH:16][N:15]=[C:9]([C:7](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11]

参加物

5

反応物 2

HCID 2736461Ethyl 3-oxo-3-(pyridin-2-yl)propanoateHCID 23668193Sodium Nitrite

生成物 1

HCID 178472895HCID 178472895、化合物収率 61.5%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒2 回

実験手順

To a stirred solution of ethyl picolinoylacetate (0.500 g, 2.6 mmol) in acetic acid (0.5 mL) was added a solution of sodium nitrite (0.238 g, 3.4 mmol) in water (0.5 mL), dropwise. The resulting solution was stirred at room temperature for 2 hours after which water (0.5 mL) was added and the reaction was stirred for a further 2 hours. The mixture was extracted with Et2O and the combined organic phase was washed with water, saturated sodium bicarbonate solution and brine, dried over MgSO4 and the solvent removed in vacuo to afford ethyl 2-(hydroxyimino)-3-oxo-3-(pyridin-2-yl)propanoate (0.353 g, 1.6 mmol, 61%) as a white solid. 1H NMR (DMSO) δ 1.17 (3H, t), 4.22 (2H, q), 7.74 (1H, m), 8.04-8.11 (2H, m), 8.74 (1H, m), 12.87 (1H, s). LCMS (2) Rt: 1.09 min; m/z (ES+) 223.

後処理

  1. additionwas added
  2. extractionThe mixture was extracted with Et2O
  3. washthe combined organic phase was washed with water, saturated sodium bicarbonate solution and brine
  4. dry with materialdried over MgSO4
  5. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-4540f02f705b4cc6b8531fc74e77a5ee
出典データセット
uspto-grants-2015_11
特許番号
US09187465B2

関連ノート

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