Hydrochloric Acid → 5-(Benzyloxy)-4,4-dimethyl-3-oxopentanenitrile

HRID 2069117Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2069117
[H-].[Na+].[CH2:3]([O:10][CH2:11][C:12]([CH3:18])([CH3:17])[C:13]([O:15]C)=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:19](#[N:21])[CH3:20].Cl>C1(C)C=CC=CC=1>[CH2:3]([O:10][CH2:11][C:12]([CH3:18])([CH3:17])[C:13](=[O:15])[CH2:20][C:19]#[N:21])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 59267989Methyl 3-(benzyloxy)-2,2-dimethylpropanoate

Produkt 1

HCID 585647415-(Benzyloxy)-4,4-dimethyl-3-oxopentanenitrileAusbeute 120,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

To a suspension of sodium hydride (1.62 g of a 60% w/w dispersion in mineral oil, 40.5 mmol) in toluene (20 mL) at reflux was added a solution of methyl 3-(benzyloxy)-2,2-dimethylpropanoate [Eur. J. Org. Chem., 2007 (6) 934-942] (6.00 g, 27.0 mmol) and acetonitrile (2.12 ml, 40.5 mmol) in toluene, dropwise over 1 hr. The reaction mixture was heated for a further 5 hr at reflux then cooled to RT. The mixture was acidified to pH 4 with aqueous hydrochloric acid (1M) and extracted with EtOAc. The organic extract was washed with water and with brine then dried (MgSO4) and evaporated in vacuo to afford 5-(benzyloxy)-4,4-dimethyl-3-oxopentanenitrile as a yellow oil (7.50 g, 96%): m/z 232 (M+H)+ (ES+), which was used without purification in the next step.

Aufarbeitung

  1. temperatureat reflux
  2. temperatureThe reaction mixture was heated for a further 5 hr
  3. temperatureat reflux
  4. extractionextracted with EtOAc
  5. extractionThe organic extract
  6. washwas washed with water and with brine
  7. dry with materialthen dried (MgSO4)
  8. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ff11871b1c184625be27e8a958e2814e
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299074B2

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