Water → 2-Di-n-propylamino-8-(2-trimethylsilylethynyl)-1,2,3,4-tetrahydronaphthalene

HRID 22143Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 22143
[CH2:1]([N:4]([CH2:16][CH2:17][CH3:18])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8](I)[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3].[CH3:19][Si:20]([C:23]#[CH:24])([CH3:22])[CH3:21].O>C(N(CC)CC)C.[Cu]I.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>[CH2:1]([N:4]([CH2:16][CH2:17][CH3:18])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([C:24]#[C:23][Si:20]([CH3:22])([CH3:21])[CH3:19])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3]

Komponenten

7

Edukt 3

HCID 962WaterHCID 66111TrimethylsilylacetyleneHCID 233735392-Di-n-propylamino-8-iodo-1,2,3,4-tetrahydronaphthalene

Produkt 1

HCID 100421182-Di-n-propylamino-8-(2-trimethylsilylethynyl)-1,2,3,4-tetrahydronaphthalene

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 2-di-n-propylamino-8-iodo-1,2,3,4-tetrahydronaphthalene (4.3 g, 12.1 mmol) in triethylamine (100 ml) was added copper(I) iodide (228 mg), bis(triphenylphosphine)palladium(II) chloride (841 mg) and trimethylsilylacetylene (1.7 ml). This mixture was stirred at room temperature overnight. The reaction was poured into water and extracted with ether. The extract was washed with brine, dried (Na2SO4), and concentrated to give 5 g of crude product. Purification by flash chromatography using 20:1 methylene chloride:methanol as solvent gave 4.33 g of 2-di-n-propylamino-8-(2-trimethylsilylethynyl)-1,2,3,4-tetrahydronaphthalene which was used in the next reaction.

Aufarbeitung

  1. extractionextracted with ether
  2. washThe extract was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto give 5 g of crude product
  6. customPurification by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-01693ebdc6c24949ada3b48f1af18635
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05426226

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