Water → 1-(2-fluoro-4-nitrophenyl)-2,3-dihydro-1H-pyridin-4-one

HRID 723897

반응식

HRID 723897 반응식
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH:15]=[C:14]([O:17][Si](C)(C)C)[CH2:13][CH2:12]1.C(=O)(OC)OCC=C.O>CS(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH:12]=[CH:13][C:14](=[O:17])[CH2:15][CH2:16]1

참가 물질

6

반응물 3

HCID 962WaterHCID 534788Methyl 2-propen-1-yl carbonateHCID 218781391-(2-Fluoro-4-nitrophenyl)-4-[(trimethylsilyl)oxy]-1,2,3,6-tetrahydropyridine

생성물 1

HCID 218776411-(2-fluoro-4-nitrophenyl)-2,3-dihydro-1H-pyridin-4-one수율 70.5%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 679Dimethyl Sulfoxide용매

실험 절차

To a stirring solution of 1-(2-fluoro-4-nitrophenyl)-4-[(trimethylsilyl)oxy]-1,2,3,6-tetrahydropyridine (Step 2, 100.0 g, 322 mmol) and allyl methyl carbonate (43.6 g, 386 mmol) in DMSO (625 ml) at ambient temperature is added Pd(OAc)2 (7.20 g, 32 mmol). The resulting solution is stirred under N2 at ambient temperature overnight. H2O (1 liter) is added and solvent allowed to cool to ambient temperature. The aqueous layer is extracted with EtOAc (2×800 ml), and the combined organic layers are washed with saline (800 ml) and dried over MgSO4. The solvent is removed and the residue recrystallized from EtOAc/MTBE to afford 53.6 g (70%) of the title compound as a yellow solid, 1H NMR (CDCl3) δ 2.71 (m, 2H), 4.06 (m, 2H), 5.41 (d, 1H), 7.25 (m, 1H), 7.35 (d, 1H), 8.08 (m, 2H).

후처리

  1. temperatureto cool to ambient temperature
  2. extractionThe aqueous layer is extracted with EtOAc (2×800 ml)
  3. washthe combined organic layers are washed with saline (800 ml)
  4. dry with materialdried over MgSO4
  5. customThe solvent is removed
  6. customthe residue recrystallized from EtOAc/MTBE

출처 및 근거

ORD 기록
ord-d437a2d51de24f5bb21a31917b36859e
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141588B2

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