Diisobutylaluminum hydride → (2,5-Dimethylfuran-3-yl)methanol

HRID 1195917

Reaktionsgleichung

Reaktionsgleichung von HRID 1195917
[C:1]([C:5]1[CH:9]=[C:8]([CH3:10])[O:7][C:6]=1[CH3:11])(OC)=[O:2].CC(C[AlH]CC(C)C)C>C(Cl)Cl>[CH3:11][C:6]1[O:7][C:8]([CH3:10])=[CH:9][C:5]=1[CH2:1][OH:2]

Komponenten

4

Edukt 2

HCID 14487Diisobutylaluminum hydrideHCID 802483-Furancarboxylic acid, 2,5-dimethyl-, methyl ester

Produkt 1

HCID 10396847(2,5-Dimethylfuran-3-yl)methanolAusbeute 63,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-carbomethoxy-2,5-dimethylfuran (2.5 g, 16.2 mmol) in methylene chloride (distilled from CaH) at -20° C., under N2, was added 2.5 eq of DIBAL (1M in CH2Cl2). After 1 h, the dry ice/acetonitrile bath was removed and 60 mL of 10% HCl was added dropwise. The organic layer was separated, dried over MgSO4, and evaporated. The residue was chromatographed (silica gel, 60% ether/hexane) to yield 1.3 g of 2,5-dimethyl-3- hydroxymethylfuran.

Aufarbeitung

  1. customthe dry ice/acetonitrile bath was removed
  2. addition60 mL of 10% HCl was added dropwise
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was chromatographed (silica gel, 60% ether/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-f6ac591abb914eab81323a78a007bd58
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05112848

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