(3-Aminopropyl)triethoxysilane → HCID 178476784、化合物

HRID 420103ノート

反応式

HRID 420103 の反応式
I[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1.[PH2:16]([O-:18])=[O:17].[NH3+][C:20]1C=CC=C[CH:21]=1.NCCC[Si](OCC)(OCC)OCC.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C.C(OCC)(=O)C.Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:13][C:12]([F:15])([F:14])[C:4]1[CH:3]=[C:2]([PH:16](=[O:18])[O:17][CH2:20][CH3:21])[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=1

参加物

9

反応物 4

HCID 13521(3-Aminopropyl)triethoxysilaneHCID 812191,3-Bis(diphenylphosphino)propaneHCID 6309701-Iodo-3,5-bis(trifluoromethyl)benzeneHCID 178527020HCID 178527020、化合物

生成物 1

HCID 178476784HCID 178476784、化合物収率 52%

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 313Hydrochloric Acid溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a degassed solution of 1-iodo-3,5-bistrifluoromethylbenzene (10.0 g, 29.4 mmol), anilinium hypophosphite (5.62 g, 35.3 mmol) and 3-aminopropyl triethoxysilane (7.81 g, 35.3 mmol) in anhydrous acetonitrile (200 mL) were added palladium acetate (132 mg, 0.588 mmol, 2 mol %) and 1,3-bis(diphenylphosphino)propane (267 mg, 0.647 mol, 2.2 mol %). The mixture was heated under reflux overnight, then cooled down to room temperature, diluted with ethyl acetate and hydrochloric acid (1M), and partitioned. The aqueous layer was further extracted with ethyl acetate and the combined extracts were washed with aqueous sodium hydrogen carbonate and brine, and dried over sodium sulfate. The volatiles were removed in vacuo, and the residue was purified by column chromatography using 30 to 70% ethyl acetate in petroleum ether to afford compound AZ3 (4.65 g) as a cloudy oil in 52% yield.

後処理

  1. temperatureThe mixture was heated
  2. temperatureunder reflux overnight
  3. custompartitioned
  4. extractionThe aqueous layer was further extracted with ethyl acetate
  5. washthe combined extracts were washed with aqueous sodium hydrogen carbonate and brine
  6. dry with materialdried over sodium sulfate
  7. customThe volatiles were removed in vacuo
  8. customthe residue was purified by column chromatography
  9. customto afford compound AZ3 (4.65 g) as a cloudy oil in 52% yield

出典と根拠

ORDレコード
ord-b0de8d3666f940fb9a127ed395dbf88e
出典データセット
uspto-grants-2012_01
特許番号
US08093379B2

反応ノート

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