Piperidine → 1-[2-(4-Trimethylsilanylethynyl-phenoxy)-ethyl]-pyrrolidine

HRID 1916755ノート

反応式

HRID 1916755 の反応式
I[C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[C:16]([Si:18]([CH3:21])([CH3:20])[CH3:19])#[CH:17].N1CCCCC1>[Cu]I>[CH3:19][Si:18]([C:16]#[C:17][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1)([CH3:21])[CH3:20]

参加物

5

反応物 3

HCID 8082PiperidineHCID 66111TrimethylsilylacetyleneHCID 219591661-(2-(4-Iodophenoxy)ethyl)pyrrolidine

生成物 1

HCID 673634551-[2-(4-Trimethylsilanylethynyl-phenoxy)-ethyl]-pyrrolidine

試薬・触媒・溶媒 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒

実験手順

Under a nitrogen atmosphere and while cooling with ice a reaction mixture of 1.5 g (4.72 mmol) 1-[2-(4-iodo-phenoxy)-ethyl]-pyrrolidine, 0.735 ml (5.2 mmol) ethynyl-trimethyl-silane, 15 mL piperidine, 115.5 mg (0.1 mmol) tetrakis-triphenylphosphane-palladium and 19 mg (0.1 mmol) CuI is stirred for 1 h. Then the reaction mixture is evaporated down, the residue is taken up in 20 mL water and extracted with EtOAc. The organic phase is dried over Na2SO4. The purification is carried out by column chromatography on silica gel (EtOAc/MeOH/NH3 95:5:0.5).

後処理

  1. temperatureUnder a nitrogen atmosphere and while cooling with ice
  2. customThen the reaction mixture is evaporated down
  3. extractionextracted with EtOAc
  4. dry with materialThe organic phase is dried over Na2SO4
  5. customThe purification

出典と根拠

ORDレコード
ord-0de9a844d51c4d5eaf0ee3bf9f794ecd
出典データセット
uspto-grants-2013_12
特許番号
US08618132B2

反応ノート

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