Hexen-2-al → Diethyl 4-n-propylpyridine-2,3-dicarboxylate

HRID 1107361

반응식

HRID 1107361 반응식
Cl[CH:2]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:15][C:16](=O)[CH:17]=[CH:18][CH2:19][CH3:20].S(=O)(=O)([O-])[NH2:23].[NH4+]>C(O)C>[CH2:17]([C:18]1[CH:19]=[CH:20][N:23]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:16][CH3:15]

참가 물질

5

반응물 3

HCID 12990Hexen-2-alHCID 24482Ammonium sulfamateHCID 10998635Diethyl 2-chloro-3-oxobutanedioate

생성물 1

HCID 22462372Diethyl 4-n-propylpyridine-2,3-dicarboxylate수율 21%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of diethyl 3-chloro-2-oxosuccinate (137.4 g, 0.69 mol), hexen-2-a1 (72.5 g, 0.74 mol) and ammonium sulphamate (190.2 g, 1.66 mol) in ethanol (450 ml) was stirred under reflux for 36 hours and then filtered. The filtrate was evaporated under vacuum, the resulting residue dissolved in water (500 ml) and this solution extracted with ethyl acetate (6×500 ml). The combined organic extracts were dried (MgSO4) and evaporated under vacuum, then the resulting residue was chromatographed on silica gel (50 g), using an ethyl acetate in hexane elution gradient (0-20% ethyl acetate), to give the title compound as an orange oil (34.1 g, 21%). Rf 0.20 (ethyl acetate:hexane, 20:80).

후처리

  1. temperatureunder reflux for 36 hours
  2. filtrationfiltered
  3. customThe filtrate was evaporated under vacuum
  4. dissolutionthe resulting residue dissolved in water (500 ml)
  5. extractionthis solution extracted with ethyl acetate (6×500 ml)
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. customevaporated under vacuum
  8. customthe resulting residue was chromatographed on silica gel (50 g)
  9. washan ethyl acetate in hexane elution gradient (0-20% ethyl acetate)

출처 및 근거

ORD 기록
ord-151897b3c8374b6da90cda72d629cc56
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06060477

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