Trimethylsilylacetylene → 2-Isopropoxy-5-((trimethylsilyl)ethynyl)benzonitrile

HRID 1522997Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1522997
Br[C:2]1[CH:3]=[CH:4][C:5]([O:10][CH:11]([CH3:13])[CH3:12])=[C:6]([CH:9]=1)[C:7]#[N:8].[CH3:14][Si:15]([CH3:19])([CH3:18])[C:16]#[CH:17]>O1CCCC1.[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>[CH:11]([O:10][C:5]1[CH:4]=[CH:3][C:2]([C:17]#[C:16][Si:15]([CH3:19])([CH3:18])[CH3:14])=[CH:9][C:6]=1[C:7]#[N:8])([CH3:13])[CH3:12]

Komponenten

6

Edukt 2

HCID 66111TrimethylsilylacetyleneHCID 32624945-Bromo-2-isopropoxybenzonitrile

Produkt 1

HCID 696691932-Isopropoxy-5-((trimethylsilyl)ethynyl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 5-bromo-2-isopropoxybenzonitrile (1.0 g, 4.16 mmol) in tetrahydrofuran was treated with copper (I) iodide (0.158 g, 0.83 mmol) and then purged with Argon for 5 minutes. Trimethyl silyl acetylene (2.85 g, 29.16 mmol) was then added followed by dichlorobis-(triphenylphosphine)palladium(II) (0.291 g, 0.41 mmol). The resultant mixture was heated at 80° C. overnight in a sealed tube. The mixture was evaporated and purified by column chromatography to give 2-isopropoxy-5-((trimethylsilyl)ethynyl)benzonitrile which was taken to the next step. 2-isopropoxy-5-((trimethylsilyl)ethynyl)benzonitrile (1.0 g, 3.8 mmol) in methanol (20 mL) was treated with potassium carbonate (1.07 g, 7.7 mmol) at room temperature overnight. The reaction was filtered and the filtrate was evaporated to give the crude product. The crude product was purified on a column (MPLC) using hexane:ethyl acetate and afforded Intermediate 1.

Aufarbeitung

  1. custompurged with Argon for 5 minutes
  2. customThe mixture was evaporated
  3. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-130b036dd7e04656b1390dabab8db778
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079864B2

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