Hydrochloric Acid → 4-Fluoro-4-methyl-3-oxopentanenitrile

HRID 929976Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 929976
[H-].[Na+].[F:3][C:4]([CH3:10])([CH3:9])[C:5](OC)=[O:6].[C:11](#[N:13])[CH3:12].Cl>C1COCC1.O>[F:3][C:4]([CH3:10])([CH3:9])[C:5](=[O:6])[CH2:12][C:11]#[N:13]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 9793744Methyl 2-Fluoro-2-methylpropionate

Produkt 1

HCID 866535074-Fluoro-4-methyl-3-oxopentanenitrileAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a stirred suspension of 60% NaH/mineral oil (12.48 g, 0.31 mol) in dry THF at 75° C. was added dropwise methyl 2-fluoro-2-methylpropanoate (24 g, 0.2 mol) in dry acetonitrile (16 mL, 0.31 mol) over the course of 45 min. The resulting pale yellow suspension was heated at 70° C. overnight, whereupon analysis by TLC indicated a single new product. After cooling to rt, the mixture was poured into water, acidified to pH˜2 with 2N HCl, and extracted with diethyl ether (1 L). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 0-30% EtOAc in petroleum ether to afford 4-fluoro-4-methyl-3-oxopentanenitrile as a colorless oil (18 g, 72% yield). LC-MS (ESI) m/z 128 (M−H)+.

Aufarbeitung

  1. temperatureAfter cooling to rt
  2. extractionextracted with diethyl ether (1 L)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 0-30% EtOAc in petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-a89e905e24e74df6a1a83b6240b9ad57
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296722B2

Notizen zur Reaktion

Wird geladen…