Tetrahydrofuran → (4-(2-Furan-2-yl-ethyl)-phenyl)-methanol

HRID 1693982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1693982
O1CCCC1.C([O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)=[CH:12][C:11]=1CC)C.[H-].C([Al+]CC(C)C)C(C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C(OCC)(=O)C>[O:19]1[CH:20]=[CH:21][CH:22]=[C:18]1[CH2:17][CH2:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][OH:8])=[CH:15][CH:14]=1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 9855836Potassium sodium tartarateHCID 21225700DiisobutylaluminumhydrideHCID 66707797Ethyl 4-(2-furan-2-yl-ethyl)-benzoic acid ethyl ester

Produkt 1

HCID 59255362(4-(2-Furan-2-yl-ethyl)-phenyl)-methanolAusbeute 99,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To an anhydrous tetrahydrofuran (10 mL) solution of ethyl 4-(2-furan-2-yl-ethyl)-benzoic acid ethyl ester (706 mg, 2.89 mmol) described in Manufacturing Example 80-1-2 was added diisobutyl aluminum hydride (0.97 M toluene solution, 7.45 mL, 7.23 mmol) on a dry ice-ethanol bath (−78° C.) under nitrogen atmosphere. After 30 minutes of stirring, 15% aqueous potassium sodium tartrate solution (40 mL) was added to the reaction solution, and stirred for 30 minutes at room temperature. Ethyl acetate (100 mL) was added, and the organic layer and water layer were separated. The organic layer was washed with water and saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure to obtain the title compound (580 mg, 99%).

Aufarbeitung

  1. stirringstirred for 30 minutes at room temperature
  2. customthe organic layer and water layer were separated
  3. washThe organic layer was washed with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-071eba30f76641a2afe3e13409eed53e
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158657B2

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