乙醇 → 6-Iodopyridine-3-carboxylic acid ethyl ester

HRID 1225

反应方程式

HRID 1225 反应方程式
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.Cl.CN(C)[CH2:14][CH2:15]CN=C=NCC.C(O)C>ClCCl.CN(C)C1C=CN=CC=1>[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:14][CH3:15])=[O:7])=[CH:4][N:3]=1

参与物

6

反应物 3

HCID 702乙醇HCID 8190626-碘烟酸HCID 27239391-乙基-(3-二甲基氨基丙基)碳酰二亚胺盐酸盐

产物 1

HCID 108911366-Iodopyridine-3-carboxylic acid ethyl ester

试剂、催化剂与溶剂 2

HCID 142844-二甲氨基吡啶(DMAP)催化剂HCID 6344二氯甲烷溶剂2 次

反应条件

温度
50 °C

实验过程

To a suspension of 23.38 g (94.2 mmol) of 6-iodonicotinic acid in 100 ml of dichloromethane was added a solution of 19.86 g (103.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in 250 ml of dichloromethane. To this suspension was added 12.40 g (15.8 ml, 269.3 mmol) of ethanol (95%) and 1.15 g (9.4 mmol) of 4-dimethylaminopyridine. The resulting solution mixture was then heated at 50° C. in an oil bath for 24.5 hours, concentrated in vacuo, partitioned between 200 ml of water and 250 ml of ethyl ether, and the layers were separated. The aqueous phase was washed with 2×150 ml-portions of ethyl ether. All organic phases were combined, washed once with 75 ml of brine solution, dried over MgSO4, filtered and concentrated in vacuo to a yellow solid. Purification by flash chromatography (silica, 10% ethyl acetate in hexane) yielded the title compound as a white solid.

后处理

  1. concentrationconcentrated in vacuo
  2. custompartitioned between 200 ml of water and 250 ml of ethyl ether
  3. customthe layers were separated
  4. washThe aqueous phase was washed with 2×150 ml-portions of ethyl ether
  5. washwashed once with 75 ml of brine solution
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to a yellow solid
  9. customPurification by flash chromatography (silica, 10% ethyl acetate in hexane)

来源与证据

ORD记录
ord-2fe08cc9e6c748808fe5a8679bdd3bfb
来源数据集
uspto-grants-1998_03
专利号
US05723620

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