Tetrahydrofuran → 1-(5-Fluoropyrimidin-2-yl)ethanone

HRID 75959Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 75959
[F:1][C:2]1[CH:3]=[N:4][C:5](C#N)=[N:6][CH:7]=1.[CH2:10]1[CH2:14][O:13]CC1.C[Mg+].[Br-]>CCOCC>[F:1][C:2]1[CH:3]=[N:4][C:5]([C:14](=[O:13])[CH3:10])=[N:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 441818675-Fluoropyrimidine-2-carbonitrileHCID 178418689HCID 178418689, Verbindung

Produkt 1

HCID 509948151-(5-Fluoropyrimidin-2-yl)ethanoneAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A round-bottom-flask containing 5-fluoropyrimidine-2-carbonitrile (Method 59, 1.50 g, 12.19 mmol) was charged with anhydrous THF (30 ml) under N2. The solution was cooled to 0° C., and a solution of MeMgBr (4.90 ml of a 3.0 M solution in ether, 14.62 mmol) was added dropwise. After 2 hours at 0° C., the reaction mixture was quenched with ice water and extracted with EtOAc. The organic extract was washed with brine, dried over Na2SO4, and evaporated to dryness to give the title compound as an oil (0.778 g, yield 46%). GC-MS, 140 (M); 1H NMR (CDCl3) δ 8.65 (s, 2H), 2.65 (s, 2H).

Aufarbeitung

  1. customthe reaction mixture was quenched with ice water
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-e02d8402bf2d48dd86d4dd21e0cc7fff
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835465B2

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