氯化铵 → 4-Methoxy-3-(3,3,3-trifluoropropyl)benzaldehyde dimethyl acetal

HRID 23763

反应方程式

HRID 23763 反应方程式
[Mg].I[CH2:3][CH2:4][C:5]([F:8])([F:7])[F:6].[Cl-].[NH4+].[CH3:11][O:12][CH:13]([O:22][CH3:23])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1>C1COCC1.[Cu]I.C(OCC)(=O)C>[CH3:11][O:12][CH:13]([O:22][CH3:23])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([CH2:3][CH2:4][C:5]([F:8])([F:7])[F:6])[CH:15]=1

参与物

8

反应物 4

HCID 25517氯化铵HCID 751404-甲氧基苯甲醛二甲缩醛HCID 1561651-碘-3,3,3-三氟丙烷HCID 5462224Magnesium2 次

产物 1

HCID 225748774-Methoxy-3-(3,3,3-trifluoropropyl)benzaldehyde dimethyl acetal

试剂、催化剂与溶剂 3

HCID 24350碘化亚铜催化剂HCID 8028四氢呋喃溶剂HCID 8857乙酸乙酯溶剂

反应条件

温度
60 °C

实验过程

A solution of 229A (15.8 g, 60 mmol) in dry THF (120 ml) was added to magnesium turnings (4.1 g, 170 mmol) at RT. The mixture was heated to 60° C. for 5 min, which initiated an exothermic reaction. The heating bath was removed and the mixture was allowed to reflux gently. Upon subsidence of the reaction (approximately 5 min), the mixture was heated to reflux for an additional 20 min and then was allowed to cool to RT. The clear green supernatant was transferred via canula away from excess magnesium and into a separate flask containing copper (I) iodide (575 mg, 3.0 mmol) under a nitrogen atmosphere. To this mixture was added 1-iodo-3,3,3-trifluoropropane (15 g, 67 mmol) and the resulting mixture was allowed to stir for 16 h, during which time a thick white precipitate developed. Aqueous ammonium chloride solution, ethyl acetate, and hexanes were added, and the organic layer was dried over sodium sulfate. Evaporation followed by silica gel chromatography of the residue using 3:1 hexanes/ethyl acetate as eluant provided 7.7 g of a mobile, slightly yellow oil, which was a 6:1 (mol ratio) mixture of 229B and 4-methoxybenzaldehyde dimethyl acetal, as determined by proton NMR. This mixture was used without further purification.

后处理

  1. customan exothermic reaction
  2. customThe heating bath was removed
  3. temperatureto reflux gently
  4. customUpon subsidence of the reaction (approximately 5 min)
  5. temperaturethe mixture was heated
  6. temperatureto reflux for an additional 20 min
  7. temperatureto cool to RT
  8. dry with materialthe organic layer was dried over sodium sulfate
  9. customEvaporation
  10. customprovided 7.7 g of a mobile, slightly yellow oil, which
  11. customThis mixture was used without further purification

来源与证据

ORD记录
ord-d9eb0245558744d682333873e1224ef1
来源数据集
uspto-grants-2005_02
专利号
US06852745B2

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