Dimethylformamide → Benzaldehyde, 2-(3-butenyl)-

HRID 921197Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 921197
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH:10]=[CH2:11].[Li]CCCC.CN(C)[CH:19]=[O:20]>C1COCC1>[CH2:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH:19]=[O:20])[CH2:9][CH:10]=[CH2:11]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 34857122-(But-3-en-1-yl)bromobenzeneHCID 178418339Butyllithium

Produkt 1

HCID 10261375Benzaldehyde, 2-(3-butenyl)-Ausbeute 92,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 1-bromo-2-(but-3-en-1-yl)benzene (1 g, 4.74 mmol) in THF (10 mL) at −78° C. was added BuLi (2.274 mL, 5.68 mmol) dropwise. It was then stirred at this temperature for 1 h, then N,N-dimethylformamide (0.416 g, 5.68 mmol) was added. The reaction was stirred at 78° C. for 30 min, then warmed to rt and stirred at rt for 1 h. It was then quenched with NH4Cl, extracted with ether. The organic layer was then dried over MgSO4, filtered and concentrated. The residue was purified by biotage, eluting with 10% EtOAc/hexane to obtain 2-(but-3-en-1-yl)benzaldehyde (0.7 g, 92%) as an oil. 1H NMR (400 MHz, CDCl3) δ 10.35-10.26 (m, 1H), 7.86 (dd, J=7.6, 1.5 Hz, 1H), 7.54 (td, J=7.5, 1.6 Hz, 1H), 7.44-7.38 (m, 1H), 7.30 (d, J=8.1 Hz, 1H), 5.95-5.83 (m, 1H), 5.09-5.00 (m, 2H),), 3.20-3.12 (m, 2H), 2.44-2.36 (m, 2H).

Aufarbeitung

  1. stirringThe reaction was stirred at 78° C. for 30 min
  2. stirringstirred at rt for 1 h
  3. customIt was then quenched with NH4Cl
  4. extractionextracted with ether
  5. dry with materialThe organic layer was then dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by biotage
  9. washeluting with 10% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-e27700a3db974338b81185866d2d5676
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273067B2

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