Diisopropylamine → 1-(4-Trimethylsilanylethynylphenyl)propan-1-one

HRID 244382

反応式

HRID 244382 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:4][CH:3]=1.[C:12]([Si:14]([CH3:17])([CH3:16])[CH3:15])#[CH:13].C(NC(C)C)(C)C>O1CCCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:15][Si:14]([C:12]#[C:13][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:4][CH:3]=1)([CH3:17])[CH3:16]

参加物

8

反応物 3

HCID 7912DiisopropylamineHCID 66111TrimethylsilylacetyleneHCID 66312p-Bromopropiophenone

生成物 1

HCID 673631271-(4-Trimethylsilanylethynylphenyl)propan-1-one

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 1.74 g 4′-bromopropiophenone, 2.0 g ethynyltrimethylsilane, 260 mg bis(triphenylphosphine)palladium(II) dichloride, 260 mg copper(I) iodide and 15 ml diisopropylamine in 40 ml tetrahydrofuran is heated at reflux for 1 h. After cooling the reaction mixture is diluted with water and extracted with ethyl acetate. The combined organic layer is washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue is purified by chromatography on silica gel, using a mixture of heptane/ethyl acetate 9:1 as eluent to obtain 1-(4-trimethylsilanylethynylphenyl)propan-1-one, m.p. 36-37° C.

後処理

  1. temperatureis heated
  2. temperatureat reflux for 1 h
  3. temperatureAfter cooling the reaction mixture
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layer is washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue is purified by chromatography on silica gel
  9. additiona mixture of heptane/ethyl acetate 9:1 as eluent

出典と根拠

ORDレコード
ord-3b2f550dab3f4c0b9c363fa1b256f8ef
出典データセット
uspto-grants-2014_02
特許番号
US08658644B2

関連ノート

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