Pivalaldehyde → HCID 22009516, Verbindung

HRID 322030Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 322030
Br[C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([F:8])=[N:6][CH:7]=1.C([Li])CCC.CC(C)(C)[CH:17]=[O:18]>CCOCC>[F:8][C:5]1[N:6]=[CH:7][C:2]([CH2:17][OH:18])=[CH:3][C:4]=1[CH3:9]

Komponenten

5

Edukt 3

HCID 12417PivalaldehydeHCID 120569025-Bromo-2-fluoro-3-methylpyridineHCID 178418339Butyllithium

Produkt 1

HCID 22009516HCID 22009516, VerbindungAusbeute 103,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

5-Bromo-2-fluoro-3-methylpyridine (2.0 g, 0.011 mol) was dissolved with stirring in anhydrous ether (30 mL) and cooled to −70° C. This was treated at <−60° C. with n-butyl lithium (4.8 mL, 2.5M in hexane, 0.012 mol) and the reaction mixture stirred at <−70° C. for one hour. Trimethylacetaldehyde (1.14 g, 0.013 mol) was added and the reaction mixture allowed to warm to −10° C. The reaction mixture was quenched with ammonium chloride solution and extracted with ethyl acetate. The organic extract was washed with water and brine, dried (Na2SO4) and evaporated to dryness. Purification of the residue by chromatography over silica (5-25% ethyl acetate:hexane) gave the desired product (1.6 g, 77%) as a clear oil.

Aufarbeitung

  1. temperatureto warm to −10° C
  2. customThe reaction mixture was quenched with ammonium chloride solution
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated to dryness
  8. customPurification of the residue by chromatography over silica (5-25% ethyl acetate:hexane)

Quellen und Nachweise

ORD-Eintrag
ord-33185891b54946c7a2bc831739e70285
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211202B1

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