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

HRID 362618

反应方程式

HRID 362618 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+]>CCOC(C)=O>[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

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-pyridinemethanol (8.0 g, 55.9 mmol), NBS (14.9 g, 83.9 mmol), and K2CO3 (11.75 g, 97.1 mmol) in EtOAc was refluxed for 3 h. A second portion of NBS (14.9 g, 83.9 mmol) and Na2CO3 (12.0 g, 114 mmol) were added and the reaction was heated to reflux for an additional 3.5 h, cooled and filtered through a pad of celite. The filtrate, after concentrattion to a small volume, was subjected to flash chromatography eluting with 0.5-4% CH3OH/CH2Cl2. The fractions containing product were combined, washed successively with sat aq NaHCO3, 10% Na2S2O3, and brine, dried (MgSO4) and concentrated in vacuo to give the title compound as a light yellow solid; yield 5.3 g (67%). 1H NMR (CDCl3) δ10.06 (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. temperaturethe reaction was heated
  3. temperatureto reflux for an additional 3.5 h
  4. temperaturecooled
  5. filtrationfiltered through a pad of celite
  6. washeluting with 0.5-4% CH3OH/CH2Cl2
  7. additionThe fractions containing product
  8. washwashed successively with sat aq NaHCO3, 10% Na2S2O3, and brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated in vacuo

来源与证据

ORD记录
ord-20c0eae67f40479784f43ae9df7def72
来源数据集
uspto-grants-1999_02
专利号
US05869660

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