Isopropyl iodide → 2-Methyl-2-[4-(propan-2-yloxy)phenyl]propanenitrile

HRID 481512Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 481512
Cl.Cl.[C:3]([C:5]([C:9]1[CH:10]=[CH:11][C:12]([O:29]C)=[C:13]([CH:28]=1)CN[C@H]1CCCN[C@H]1C1C=CC=CC=1)([C:7]#N)[CH3:6])#[N:4].I[CH:32]([CH3:34])[CH3:33].C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)=O.CCOC(C)=O>[CH:32]([O:29][C:12]1[CH:11]=[CH:10][C:9]([C:5]([CH3:7])([CH3:6])[C:3]#[N:4])=[CH:28][CH:13]=1)([CH3:34])[CH3:33]

Komponenten

6

Edukt 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 86752971(2S,3S)-3-(5-(1,1-dicyanoethyl)-2-methoxybenzyl)amino-2-phenylpiperidine Dihydrochloride

Produkt 1

HCID 190664532-Methyl-2-[4-(propan-2-yloxy)phenyl]propanenitrileAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of Compound 39 (500 mg, 3.10 mmol) and 2-Iodopropane (0.930 ml, 9.30 mmol) in acetone (8 ml) was added Cs2CO3 (4.55 g, 14.0 mmol), and refluxed for 2 h. The mixture was filtered over celite and washed with acetone. The filtrate was concentrated to give crude Compound 40. This was diluted with AcOEt, washed with water and brine, dried (MgSO4), and concentrated. This was purified by a column chromatography on silica gel to give Compound 40 (610 mg, 97%) as a colorless oil.

Aufarbeitung

  1. temperaturerefluxed for 2 h
  2. filtrationThe mixture was filtered over celite
  3. washwashed with acetone
  4. concentrationThe filtrate was concentrated
  5. customto give crude Compound 40
  6. washwashed with water and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThis was purified by a column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-22e1a4f6a2364c82b6fd9347eda1586c
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05789423

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