Tetrahydrofuran → Tris(4-ethynylphenyl)amine

HRID 1840695ノート

反応式

HRID 1840695 の反応式
O1CCCC1.C[Si]([C:10]#[C:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]([C:31]2[CH:36]=[CH:35][C:34]([C:37]#[C:38][Si](C)(C)C)=[CH:33][CH:32]=2)[C:19]2[CH:24]=[CH:23][C:22]([C:25]#[C:26][Si](C)(C)C)=[CH:21][CH:20]=2)=[CH:14][CH:13]=1)(C)C.[F-].[K+]>CO>[C:25]([C:22]1[CH:21]=[CH:20][C:19]([N:18]([C:15]2[CH:14]=[CH:13][C:12]([C:11]#[CH:10])=[CH:17][CH:16]=2)[C:31]2[CH:36]=[CH:35][C:34]([C:37]#[CH:38])=[CH:33][CH:32]=2)=[CH:24][CH:23]=1)#[CH:26]

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 522689Potassium FluorideHCID 23443707Tris(4-((trimethylsilyl)ethynyl)phenyl)amine

生成物 1

HCID 23443705Tris(4-ethynylphenyl)amine収率 75%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

To a mixture of 180 ml of tetrahydrofuran (THF) and 240 ml of methanol were added 13.84 g (0.026 mol) of tri(4-trimethylsilylethynylphenyl)amine and 4.53 g (0.078 mol) of potassium fluoride. The reaction mixture was heated at 50° C. for 5 h, cooled down to room temperature, and solvent was removed under the reduced pressure. The residue was extracted with ether and the ether layer was washed with distilled water. The washed ether layer was concentrated to give crude product. The crude product was purified by column chromatography on silica gel by eluting with hexane to give 6.182 g (75%) of tri(4-ethynylphenyl)amine of which NMR spectrum was shown in FIG. 9 and mp was 115° C.

後処理

  1. temperaturecooled down to room temperature
  2. customsolvent was removed under the reduced pressure
  3. extractionThe residue was extracted with ether
  4. washthe ether layer was washed with distilled water
  5. concentrationThe washed ether layer was concentrated
  6. customto give crude product
  7. customThe crude product was purified by column chromatography on silica gel
  8. washby eluting with hexane

出典と根拠

ORDレコード
ord-571735d7247149858c6a591f017d96ed
出典データセット
uspto-grants-2004_01
特許番号
US06682782B2

反応ノート

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