Water → 5-(2,2-Dimethyl-1,3-dioxolan-4-yl)pyridine-2-carbaldehyde

HRID 1881840Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1881840
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][O:11][C:10]([CH3:14])([CH3:13])[O:9]2)=[CH:4][N:3]=1.CCCCCC.C([Li])CCC.CN(C)[CH:28]=[O:29].O>C(OCC)C>[CH3:13][C:10]1([CH3:14])[O:9][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([CH:28]=[O:29])=[N:3][CH:4]=2)[CH2:12][O:11]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6228DimethylformamideHCID 469414392-Bromo-5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridineHCID 178418244HCID 178418244, Verbindung

Produkt 1

HCID 469414405-(2,2-Dimethyl-1,3-dioxolan-4-yl)pyridine-2-carbaldehydeAusbeute 27,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 2-bromo-5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridine (4.12 g) in diethyl ether (100 mL) was slowly added a 1.6M n-butyllithium hexane solution (10 mL) at −78° C. The reaction mixture was stirred for 30 min, and N,N-dimethylformamide (1.40 g) was added. The reaction mixture was warmed to room temperature over 1 hr, and stirred overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (900 mg, yield 27%) was obtained as a pale-yellow oil from a fraction eluted with ethyl acetate-hexane (1:4, volume ratio). MS: 208 (MH+).

Aufarbeitung

  1. stirringstirred overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b70778ee1ed34c809b36895e96736f5f
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318746B2

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