Methyl iodide → 2-[4-(Propan-2-yl)phenyl]propanenitrile

HRID 720550

Reaktionsgleichung

Reaktionsgleichung von HRID 720550
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#[N:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[CH3:13][Si]([N-][Si](C)(C)C)(C)C.[Li+].IC>O1CCCC1>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH3:13])[C:11]#[N:12])=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 1382224-IsopropylphenylacetonitrileHCID 2733832Lithium Hexamethyldisilazide

Produkt 1

HCID 136820102-[4-(Propan-2-yl)phenyl]propanenitrileAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

In a 250 ml flask, 4-isopropylphenylacetonitrile 8.00 g (50.2 mmol) was dissolved in tetrahydrofuran (150 ml) under a nitrogen atmosphere. The solution was cooled to −78° C. and lithium bis(trimethylsilyl)amide (1M in tetrahydrofuran, 52.8 ml (52.8 mmol) added. The resulting mixture was stirred at −78° C. for 1 hour. To this reaction mixture was added iodomethane 3.29 ml (52.8 mmol). The resulting mixture was slowly allowed to warm to ambient temperature over 16 hours then quenched with 0.2M hydrochloric acid and extracted twice with diethyl ether. The organic fractions were combined, dried (MgSO4) and concentrated under vacuo. Chromatography (SiO2, 20% ethyl acetate/hexanes) gave 6.32 g (73%) of the title compound.

Aufarbeitung

  1. temperatureto warm to ambient temperature over 16 hours
  2. customthen quenched with 0.2M hydrochloric acid
  3. extractionextracted twice with diethyl ether
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under vacuo

Quellen und Nachweise

ORD-Eintrag
ord-46df4c6e30f74d1a813ac9275cd68f9c
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07135487B2

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