Dimethylformamide → 5-Propoxypyridine-2-carboxaldehyde

HRID 1858017ノート

反応式

HRID 1858017 の反応式
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]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 221255242-Iodo-5-propoxypyridineHCID 178418306HCID 178418306、化合物

生成物 1

HCID 150502285-Propoxypyridine-2-carboxaldehyde

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d3d53baeb28745fcb4f6d01fe1a0a1ea
出典データセット
uspto-grants-2000_11
特許番号
US06150379

反応ノート

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