氯化铵 → Ethyl 4-(3,3,3-trifluoro-propylidene)-cyclohexanecarboxylate

HRID 1754980

反应方程式

HRID 1754980 反应方程式
C([Li])CCC.[I-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:14][CH2:15][C:16]([F:19])([F:18])[F:17])C=CC=CC=1.[CH2:32]([O:34][C:35]([CH:37]1[CH2:42][CH2:41][C:40](=O)[CH2:39][CH2:38]1)=[O:36])[CH3:33].[Cl-].[NH4+]>C1COCC1>[F:17][C:16]([F:19])([F:18])[CH2:15][CH:14]=[C:40]1[CH2:41][CH2:42][CH:37]([C:35]([O:34][CH2:32][CH3:33])=[O:36])[CH2:38][CH2:39]1

参与物

6

反应物 4

HCID 25517氯化铵HCID 317638对环己酮甲酸乙酯HCID 19694095三苯基(3,3,3-三氟丙基)碘化膦HCID 178418339正丁基锂

产物 1

HCID 66817607Ethyl 4-(3,3,3-trifluoro-propylidene)-cyclohexanecarboxylate收率 96%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂2 次

实验过程

n-Butyllithium (1.6 M solution in hexane, 26 ml, 41.6 mmol) was added to a solution of triphenyl-(3,3,3-trifluoro-propyl)-phosphonium iodide (20.25 g, 41.64 mmol) in THF (141 ml) at −78° C. over 13 minutes, and the mixture was stirred at the same temperature for 20 minutes. A solution of 4-oxo-cyclohexanecarboxylic acid ethyl ester (6.56 g, 38.54 mmol) in THF (22 ml) was added to the reaction solution at −78° C. over 17 minutes, and the mixture was stirred at the same temperature for one hour. A 50% saturated aqueous ammonium chloride solution was added, followed by extraction with dichloromethane. The organic layer was then dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give ethyl 4-(3,3,3-trifluoro-propylidene)-cyclohexanecarboxylate (9.25 g, 96%).

后处理

  1. stirringthe mixture was stirred at the same temperature for one hour
  2. extractionfollowed by extraction with dichloromethane
  3. dry with materialThe organic layer was then dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

来源与证据

ORD记录
ord-41355dc934384b049f88857382137aa4
来源数据集
uspto-grants-2015_10
专利号
US09169254B2

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