Halite (NaCl) → 4-三甲基硅乙炔基苯甲醛

HRID 13899

反应方程式

HRID 13899 反应方程式
C1(NC2CCCCC2)CCCCC1.Br[C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1.[CH3:23][Si:24]([C:27]#[CH:28])([CH3:26])[CH3:25].[Cl-].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu]I.C1(C)C=CC([B-](C2C=CC(C)=CC=2)(C2C=CC(C)=CC=2)C2C=CC(C)=CC=2)=CC=1.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.C1(C)C=CC=CC=1.O1CCCC1>[CH3:23][Si:24]([C:27]#[C:28][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1)([CH3:26])[CH3:25]

参与物

10

反应物 4

HCID 5234Halite (NaCl)HCID 7582二环己胺HCID 66111三甲基硅乙炔HCID 70741对溴苯甲醛

产物 1

HCID 27716434-三甲基硅乙炔基苯甲醛收率 88%

试剂、催化剂与溶剂 5

HCID 24350碘化亚铜催化剂HCID 167845palladium acetate催化剂HCID 23136639Tri-tert-butylphosphonium tetra-para-tolylborate催化剂HCID 1140甲苯溶剂HCID 8028四氢呋喃溶剂2 次

实验过程

A 50-ml four-necked flask was equipped with a stirrer, 20 a thermometer and a reflux condenser. 0.034 g (0.15 mmol) of palladium (II) acetate, 0.019 g (0.1 mmol) of copper (I) iodide, 1.088 g (6 mmol) of dicyclohexylamine and 9 ml of tetrahydrofuran were weighed in the flask, followed by stirring. Further, 0.174 g (0.3 mmol) of tri-tert-butylphosphonium tetra-para-tolylborate obtained in Example B-3 was weighed in air and added into the flask. The flask was purged with argon, followed by stirring at 30° C. for 30 minutes. 0.925 g (5 mmol) of 4-bromobenzaldehyde and 0.589 g (6 mmol) of trimethylsilylacetylene were added, followed by stirring at 30° C. for 17 hours. After the completion of the reaction, 10 ml of tetrahydrofuran, 5 ml of toluene and 15 ml of saturated sodium chloride solution were added, followed by separation. The organic phase was purified by column chromatography to afford 0.890 g of 4-[(trimethylsilyl)ethynyl]benzaldehyde (yield: 88 mol % based on 4-bromobenzaldehyde). The identification of the product was made by 1H-NMR and 13C-NMR.

后处理

  1. customA 50-ml four-necked flask was equipped with a stirrer
  2. additionadded into the flask
  3. customThe flask was purged with argon
  4. stirringby stirring at 30° C. for 30 minutes
  5. stirringby stirring at 30° C. for 17 hours
  6. additionwere added
  7. customfollowed by separation
  8. customThe organic phase was purified by column chromatography

来源与证据

ORD记录
ord-2a9c8634b37b4cc0a25fd86be7f91beb
来源数据集
uspto-grants-2010_06
专利号
US07728176B2

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