Iodoethane → 2-Methyl-2-phenylbutanenitrile

HRID 400650

Reaktionsgleichung

Reaktionsgleichung von HRID 400650
[C:1]1([CH:7]([CH3:10])[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:11]1COC[CH2:12]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C(I)C>CS(C)=O.O>[CH3:10][C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([CH2:11][CH3:12])[C:8]#[N:9]

Komponenten

7

Edukt 4

HCID 6340IodoethaneHCID 8028TetrahydrofuranHCID 157612-PhenylpropionitrileHCID 2724254Sodium bis(trimethylsilyl)amide

Produkt 1

HCID 32541802-Methyl-2-phenylbutanenitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-phenylpropionitrile (5 g, 38 mmol) in 50 mL of DMSO was added 42 mL of 1 M THF solution of sodium bis(trimethylsilyl)amide (NaHMDS). After 15 minutes, the reaction was cooled to 0° C. and 4.6 mL of ethyl iodide was added. The reaction was then stirred for 30 minutes. As TLC showed the reaction was complete, the reaction mixture was poured into water and extracted with diethyl ether. The organics were combined, washed four times with water, washed with brine, dried over magnesium sulfate, and concentrated in vacuo to give 6.1 g of 2-methyl-2-phenylbutyronitrile as an oil.

Aufarbeitung

  1. extractionextracted with diethyl ether
  2. washwashed four times with water
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-06132d039a1f4c9ab83ae7bdfc79383e
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741897B2

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