3-Acetylpyridine → Methyl 2,4-dioxo-4-(pyridin-3-yl)butanoate

HRID 8082

반응식

HRID 8082 반응식
C[O-].[Na+].CO[C:6](=[O:11])[C:7]([O:9][CH3:10])=[O:8].[C:12]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)(=[O:14])[CH3:13]>CO>[O:11]=[C:6]([CH2:13][C:12](=[O:14])[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[C:7]([O:9][CH3:10])=[O:8]

참가 물질

5

반응물 3

HCID 95893-AcetylpyridineHCID 11120Dimethyl oxalateHCID 10942334Sodium Methoxide

생성물 1

HCID 2771616Methyl 2,4-dioxo-4-(pyridin-3-yl)butanoate수율 84%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Sodium methoxide (5.4 g, 100 mmol) and dimethyloxalate (11.8 g, 100 mmol) were dissolved in anhydrous methanol (700 mL) and stirred at room temperature under nitrogen until a suspension was formed. To this mixture, 3-acetylpyridine (5.5 mL, 50 mmol) was added and the stirring was continued for 3 days at room temperature. The reaction was quenched with enough 5% aqueous KHSO4 until all solids have dissolved. The methanol was removed under reduced pressure, and the residue was extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with water (2×200 mL), brine and dried (NaSO4) followed by the removal of solvent under reduced pressure to give the title compound (8.67 g, 84% yield) as a yellow solid. 1H NMR (CDCl3, 300 MHz) δ 9.21–9.20 (m, 1H), 8.84–8.82 (m, 1H), 8.30–8.26 (m, 1H), 7.50–7.45 (m, 1H), 7.08 (s, 1H), 3.96 (s, 3H). 13C NMR (CDCl3, 75 MHz) δ 188.5, 170.4, 162.2, 153.9, 149.0, 135.2, 130.5, 123.8, 98.0, 53.3. mass spectrum (APIMS) m/z 208 (M+1)+.

후처리

  1. customwas formed
  2. customThe reaction was quenched with enough 5% aqueous KHSO4 until all solids
  3. dissolutionhave dissolved
  4. customThe methanol was removed under reduced pressure
  5. extractionthe residue was extracted with ethyl acetate (3×200 mL)
  6. washThe combined organic layers were washed with water (2×200 mL), brine
  7. dry with materialdried (NaSO4)
  8. customfollowed by the removal of solvent under reduced pressure

출처 및 근거

ORD 기록
ord-7a51bd60341c47f6bf110e2467dc0b37
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087630B2

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