Dimethylformamide → 5-(1,1-Dimethyl-allyl)-2-methoxy-benzaldehyde

HRID 1989818Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1989818
Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:12])([CH3:11])[CH:9]=[CH2:10])[CH:5]=[CH:4][C:3]=1[O:13][CH3:14].[Li]CCCC.CN([CH:23]=[O:24])C>C1COCC1>[CH3:11][C:8]([C:6]1[CH:5]=[CH:4][C:3]([O:13][CH3:14])=[C:2]([CH:7]=1)[CH:23]=[O:24])([CH3:12])[CH:9]=[CH2:10]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 112422612-Bromo-4-(1,1-dimethyl-allyl)-1-methoxy-benzeneHCID 178418339Butyllithium

Produkt 1

HCID 113331815-(1,1-Dimethyl-allyl)-2-methoxy-benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 2-Bromo-4-(1,1-dimethyl-allyl)-1-methoxy-benzene (3.1 g, 0.012 mol) in dry THF (50 mL) was cooled to −78° C. under argon. n-BuLi (2.5M, 5.1 mL, 0.0128 mol) was added keeping the temperature below −70° C. The yellow mixture was stirred for another 15 min and quenched with dry DMF (1.4 mL, 0.018 mol). The cooling bath was removed and the mixture was allowed to warm to 25° C. A saturated solution of NaHCO3 (30 mL) was added and then extracted with EtOAc (3×50 mL). The organic phase was dried (Na2SO4) and evaporated to yellow oil. Yield: 2.31 g (94%).

Aufarbeitung

  1. customthe temperature below −70° C
  2. customThe cooling bath was removed
  3. additionA saturated solution of NaHCO3 (30 mL) was added
  4. extractionextracted with EtOAc (3×50 mL)
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. customevaporated to yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-ada405e7b3eb4dd8838b9f85449f6475
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07642367B2

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