Dimethylformamide → 5-Propoxypyridine-2-carboxaldehyde

HRID 1858017노트

반응식

HRID 1858017 반응식
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][CH3:11])=[CH:4][N:3]=1.C1C[O:15][CH2:14]C1.C([Li])(C)(C)C.CN(C)C=O>O.C(OCC)(=O)C>[CH2:9]([O:8][C:5]1[CH:6]=[CH:7][C:2]([CH:14]=[O:15])=[N:3][CH:4]=1)[CH2:10][CH3:11]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 221255242-Iodo-5-propoxypyridineHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 150502285-Propoxypyridine-2-carboxaldehyde

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
-78 °C

실험 절차

A mixture comprising 2-iodo-5-propoxypyridine (0.27 g, 1 mmol) and THF (10 mL) was cooled to -78° C. and then tert-butyl lithium (1.3 mL, 1.7 M in pentane, 2.1 mmol) was added dropwise to give an orange slurry. The slurry was cooled to -78° C. and stirred for 5 minutes and then anhydrous N,N-dimethylformamide (0.4 mL, 5 mmol) was added dropwise. The mixture was allowed to warm to ambient temperature, stirred 20 minutes and then poured into a mixture comprising ethyl acetate and water. The mixture was washed with water, dried (MgSO4), filtered and concentrated under reduced pressure to provide 5-propoxypyridine-2-carboxaldehyde (0.2 g, 1.3 mmol) as a dark oil. 1H-NMR (300 Mhz, CD3OD): 1.1 (t, 3H), 1.9 (m, 2H), 4.1 (t, 2H), 7.5 (m, 2H), 8.4 (m, 1H), 10.5 (s, 2H); MS (CI); Calculated for C9H11NO2, 165.2, Found (MH+): 166.

후처리

  1. customto give an orange slurry
  2. temperatureto warm to ambient temperature
  3. stirringstirred 20 minutes
  4. washThe mixture was washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d3d53baeb28745fcb4f6d01fe1a0a1ea
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06150379

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