Carbonic acid sodium salt (1:2) → 2-氯吡啶-4-甲醛

HRID 344008

反应方程式

HRID 344008 反应方程式
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1.C1C(=O)N(Br)C(=O)C1.C([O-])([O-])=O.[K+].[K+].C([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][N:3]=1

参与物

6

反应物 4

HCID 10340Carbonic acid sodium salt (1:2)HCID 11430碳酸钾HCID 67184N-溴代丁二酰亚胺(NBS)2 次HCID 7062237(2-氯吡啶-4-基)甲醇

产物 1

HCID 27629942-氯吡啶-4-甲醛收率 67%

试剂、催化剂与溶剂 1

HCID 8857乙酸乙酯溶剂

实验过程

A suspension of 2-chloro-4-hydroxymethylpyridine (8.0 g, 55.9 mmol), NBS (14.9 g, 83.9 mmol), and K2CO3 (11.75 g, 97.1 mmol) in ethyl acetate was refluxed for 3 h. Another portion of NBS (14.9 g, 83.9 mmol) and Na2CO3 (12.0 g, 114 mmol) was added and heating was continued another 3.5 h. The reaction mixture was cooled, filtered through a pad of celite, concentrated under reduced and chromatographed with 0.5-4% CH3OH/CH2Cl2. The combined fractions were washed with NaHCO3 (sat.), 10% Na2S2O3, and NaCl (sat.), dried, filtered and evaporated to give the title compound as a light yellow solid (5.3 g, 67% yield). 1H NMR (CDCl3): δ 10.06 (s, 1H), 8.66 (d, 1H, J=5.0 Hz), 7.76 (s, 1H), 7.66 (d, 1H, J=5.0 Hz).

后处理

  1. temperaturewas refluxed for 3 h
  2. temperatureheating
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered through a pad of celite
  5. concentrationconcentrated under reduced and
  6. customchromatographed with 0.5-4% CH3OH/CH2Cl2
  7. washThe combined fractions were washed with NaHCO3 (sat.), 10% Na2S2O3, and NaCl (sat.)
  8. customdried
  9. filtrationfiltered
  10. customevaporated

来源与证据

ORD记录
ord-f12ea0af20b142048378d653f7fa356c
来源数据集
uspto-grants-1999_01
专利号
US05864036

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