Diethyl Ether → Di-3-pyridinylmethanone

HRID 742461

Reaktionsgleichung

Reaktionsgleichung von HRID 742461
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:8]([Li])[CH2:9][CH2:10][CH3:11].[CH3:13][N:14](OC)[C:15](OCC)=O.CC[O:24]CC>>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:8]([C:9]2[CH:13]=[N:14][CH:15]=[CH:11][CH:10]=2)=[O:24])[CH:3]=1

Komponenten

5

Edukt 4

HCID 3283Diethyl Ether2×HCID 122863-BromopyridineHCID 533715Ethyl N-methoxy-N-methylcarbamateHCID 178418339Butyllithium

Produkt 1

HCID 298471Di-3-pyridinylmethanoneAusbeute 33 %

Versuchsvorschrift

To a solution of 3-bromopyridine (9.84 g, 0.062 mol) in 300 mL of ether cooled to -78° C. was added n-butyllithium (1.6M, 41 mL, 0.066 mol) and stirred for 30 min. N-Methyl,N-methoxy-urethane (3.76 g, 0.028 mol) in 20 mL of ether was added in 10 min, the mixture was stirred (-78° C.) for 1 h, allowed to warm to room temperature and stirred for 2 h. The reaction mixture was quenched with 6N HCl (100 mL) and stirred. The aqueous layer was basified with 10% NaOH solution, extracted with ethyl acetate (2×) and methylene dichloride. The organic layer was dried over sodium sulfate, concentrated in vacuo, and the residue was purified by chromatography on silica (ethyl acetate, 10% methanol/ethyl acetate) to afford 1.7 g (33%) of di-(3-pyridyl)ketone.

Aufarbeitung

  1. stirringthe mixture was stirred (-78° C.) for 1 h
  2. stirringstirred for 2 h
  3. customThe reaction mixture was quenched with 6N HCl (100 mL)
  4. stirringstirred
  5. extractionextracted with ethyl acetate (2×) and methylene dichloride
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customthe residue was purified by chromatography on silica (ethyl acetate, 10% methanol/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-a84c0e5983224b928786a06dc687df70
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05554620

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