Diisopropylamine → Ethyl 3-((trimethylsilyl)ethynyl)benzoate

HRID 1760087Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1760087
Br[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:13]([Si:15]([CH3:18])([CH3:17])[CH3:16])#[CH:14].C(NC(C)C)(C)C>C1COCC1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:16][Si:15]([C:13]#[C:14][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])([CH3:18])[CH3:17]

Komponenten

6

Edukt 3

HCID 7912DiisopropylamineHCID 66111TrimethylsilylacetyleneHCID 90488Ethyl 3-bromobenzoate

Produkt 1

HCID 22600505Ethyl 3-((trimethylsilyl)ethynyl)benzoateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of ethyl 3-bromobenzoate (1.0 g, 4.37 mmol), ethynyl trimethylsilane (644 mg, 6.56 mmol), diisopropylamine (929 mg, 9.20 mmol), cuprous iodide(I) (16.6 mg, 0.0872 mmol), and bis(triphenylphosphine) palladium(II) chloride (123 mg, 0.175 mmol) was heated at 45° C. for 5 h in dried THF (8 ml) under argon atmosphere. After cooling, the reaction was quenched by the addition of water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel flash column chromatography (eluent: hexane/ethyl acetate=50/1) to give ethyl 3-[(trimethylsilyl)-ethynyl]benzoate (90%)

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe reaction was quenched by the addition of water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel flash column chromatography (eluent: hexane/ethyl acetate=50/1)

Quellen und Nachweise

ORD-Eintrag
ord-15558a6163c74d16a8d43daa9e840eec
Quelldatensatz
uspto-grants-2005_01
Patentnummer
US06838574B1

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