Hydrochloric Acid → 4,4-Dimethyl-3-oxo-5-(tetrahydro-pyran-2-yloxy)-pentanenitrile

HRID 469756Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 469756
CO[C:3](=[O:15])[C:4]([CH3:14])([CH3:13])[CH2:5][O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1.[C:16](#[N:18])[CH3:17].[H-].[Na+].Cl>C1(C)C=CC=CC=1>[CH3:14][C:4]([CH3:13])([CH2:5][O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1)[C:3](=[O:15])[CH2:17][C:16]#[N:18]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 59253280methyl 2,2-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)propanoate

Produkt 1

HCID 592532944,4-Dimethyl-3-oxo-5-(tetrahydro-pyran-2-yloxy)-pentanenitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A solution of 2,2-dimethyl-3-(tetrahydro-pyran-2-yloxy)-propionic acid methyl ester (7.67 g, 35.46 mmol) and acetonitrile (2.6 mL, 49.65 mmol) in toluene (20 mL) is added dropwise to the refluxing suspension of 60% sodium hydride in mineral oil (1.99 g, 49.65 mmol) in toluene (40 mL). After the addition, the reaction mixture is stirred at reflux for 3 hours. After this time, the reaction mixture is cooled to room temperature and the aqueous layer is neutralized to PH˜6-7 by adding 1N hydrochloric acid aqueous solution. The layers are combined and the aqueous layer is extracted with ethyl acetate. The organic layers are combined and washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to yield the title compound. It is used without purification.

Aufarbeitung

  1. additionAfter the addition
  2. temperatureat reflux for 3 hours
  3. extractionthe aqueous layer is extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-735c32d3a04f4fc0935e2f002b94f5f1
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629157B2

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