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

HRID 244382

반응식

HRID 244382 반응식
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]

참가 물질

8

반응물 3

HCID 7912DiisopropylamineHCID 66111TrimethylsilylacetyleneHCID 66312p-Bromopropiophenone

생성물 1

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

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3b2f550dab3f4c0b9c363fa1b256f8ef
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658644B2

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