Hexane → (6-(4-Fluorophenyl)hexa-1,5-diynyl)trimethylsilane

HRID 334553

Reaktionsgleichung

Reaktionsgleichung von HRID 334553
[CH3:1][Si:2]([CH3:7])([CH3:6])[C:3]#[C:4][CH3:5].[Li]CCCC.CCCCCC.Br[CH2:20][C:21]#[C:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1>C1COCC1>[F:29][C:26]1[CH:27]=[CH:28][C:23]([C:22]#[C:21][CH2:20][CH2:5][C:4]#[C:3][Si:2]([CH3:7])([CH3:6])[CH3:1])=[CH:24][CH:25]=1

Komponenten

6

Edukt 4

HCID 8058HexaneHCID 803631-(Trimethylsilyl)prop-1-yneHCID 105605241-(3-Bromoprop-1-yn-1-yl)-4-fluorobenzeneHCID 178418339Butyllithium

Produkt 1

HCID 66597810(6-(4-Fluorophenyl)hexa-1,5-diynyl)trimethylsilaneAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of trimethyl(prop-1-ynyl)silane (2.19 g, 19.50 mmol) in 22 mL of THF at −78° C., was added dropwise n-BuLi 2.5M in hexane (7.8 mL, 20 mmol). After stirring 2 hours at −78° C., 1-(3-bromoprop-1-ynyl)-4-fluorobenzene (1.40 g, 6.5 mmol) in 6 mL of THF was slowly added and the resulting mixture was stirred for 1 h at −78° C. and warmed to room temperature for an additional 1 h. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered and concentrated to afford 1.57 g of (6-(4-fluorophenyl)hexa-1,5-diynyl)trimethylsilane (99%) as a yellow oil.

Aufarbeitung

  1. stirringthe resulting mixture was stirred for 1 h at −78° C.
  2. temperaturewarmed to room temperature for an additional 1 h
  3. customThe reaction mixture was quenched with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6f4a3cd4ef624ad5944a351375f5c8fd
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883826B2

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