Diethyl Ether → 4-(Hydroxy-(5-methyl-furan-2-yl)-methyl)benzaldehyde

HRID 1691014

Reaktionsgleichung

Reaktionsgleichung von HRID 1691014
CO[CH:3]([O:11]C)[C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=1.C(OCC)C.C([Li])CCC.[CH3:23][C:24]1[O:30][C:27]([CH:28]=[O:29])=[CH:26][CH:25]=1>C(OCC)(=O)C.O>[OH:29][CH:28]([C:27]1[O:30][C:24]([CH3:23])=[CH:25][CH:26]=1)[C:7]1[CH:6]=[CH:5][C:4]([CH:3]=[O:11])=[CH:9][CH:8]=1

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 120975-MethylfurfuralHCID 6883421-Bromo-4-(dimethoxymethyl)benzeneHCID 178418339Butyllithium

Produkt 1

HCID 592553364-(Hydroxy-(5-methyl-furan-2-yl)-methyl)benzaldehydeAusbeute 12,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 4-bromobenzaldehyde dimethyl acetal (2.0 mL, 12 mmol) and diethyl ether (30 mL) was added dropwise n-butyl lithium (1.6 M n-hexane solution, 9.0 mL, 14 mmol) at −78° C., which was stirred for 20 minutes at the same temperature. 5-Methylfurfural (1.3 mL, 13 mmol) was added dropwise into the reaction mixture at that temperature, and stirred for 50 minutes at 0° C. Water and ethyl acetate were added to extract the reaction mixture. The organic layer was washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:2) to obtain the title compound (320 mg, 12%).

Aufarbeitung

  1. stirringstirred for 50 minutes at 0° C
  2. extractionto extract the reaction mixture
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. customthe solvent was evaporated under a reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-1a1839b0d51345f99fe5b6801f2fd62a
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153662B2

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