乙酰乙酸甲酯 → Methyl (E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-methoxy-3-methoxy-methyl-pyridin-5-yl]-5-hydroxy-3-oxo-hept-6-enoate

HRID 36919笔记

反应方程式

HRID 36919 反应方程式
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].[CH2:11]([Li])CCC.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:28](/[CH:29]=[CH:30]/[CH:31]=[O:32])=[C:27]([CH:33]([CH3:35])[CH3:34])[N:26]=[C:25]([O:36][CH3:37])[C:24]=2COC)=[CH:19][CH:18]=1.[O:41]1CCC[CH2:42]1>CCCCCC.CCOCC.[Cl-].[NH4+].[Cl-].[Zn+2].[Cl-]>[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[C:28](/[CH:29]=[CH:30]/[CH:31]([OH:32])[CH2:5][C:3](=[O:4])[CH2:2][C:1]([O:7][CH3:8])=[O:6])=[C:27]([CH:33]([CH3:35])[CH3:34])[N:26]([CH3:11])[CH:25]([O:36][CH3:37])[C:24]=2[O:41][CH3:42])=[CH:21][CH:22]=1

参与物

10

反应物 5

HCID 7757乙酰乙酸甲酯HCID 8028四氢呋喃2 次HCID 24758氢化钠HCID 19936689(E)-3-[4-(4-Fluorophenyl)-6-isopropyl-2-methoxy-3-methoxymethyl-pyridin-5-yl]-prop-2-enalHCID 178418339正丁基锂

产物 1

HCID 131719005Methyl (E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-methoxy-3-methoxy-methyl-pyridin-5-yl]-5-hydroxy-3-oxo-hept-6-enoate

试剂、催化剂与溶剂 4

HCID 3007855氯化锌催化剂HCID 3283乙醚溶剂HCID 8058正己烷溶剂HCID 25517氯化铵溶剂

实验过程

0.35 ml (3.3 mmol) of methyl acetoacetate are added dropwise under nitrogen to a suspension of 80 mg (3.4 mmol) of sodium hydride in 3 ml of dry tetrahydrofuran at -5° C. After 15 min, 2.3 ml (3.3 mmol) of 15% strength butyllithium in n-hexane and 3.3 ml (3.3 mmol) of a 1 molar zinc chloride solution in ether are added dropwise at the same temperature and the mixture is stirred for 15 min. 530 mg (1.5 mmol) of the compound from Example 10 dissolved in 8 ml of dry tetrahydrofuran are then added dropwise and the mixture is stirred at -5° C. for 30 min. The reaction solution is cautiously diluted with 100 ml of saturated aqueous ammonium chloride solution and the mixture is extracted three times with 100 ml of ether each time. The combined organic phases are washed twice with saturated sodium hydrogen carbonate solution and once with saturated sodium chloride solution, dried over sodium sulphate and concentrated in vacuo.

后处理

  1. additionare then added dropwise
  2. stirringthe mixture is stirred at -5° C. for 30 min
  3. extractionthe mixture is extracted three times with 100 ml of ether each time
  4. washThe combined organic phases are washed twice with saturated sodium hydrogen carbonate solution and once with saturated sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo

来源与证据

ORD记录
ord-b62755906215485e999eb3fe515012ae
来源数据集
uspto-grants-1995_05
专利号
US05418243

反应笔记

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