Ethyl 3-oxo-3-(pyridin-2-yl)propanoate → HCID 178472895, 화합물

HRID 714928

반응식

HRID 714928 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

HCID 178472895HCID 178472895, 화합물수율 61.5%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4540f02f705b4cc6b8531fc74e77a5ee
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187465B2

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