Aluminium lithium hydride → (2-Phenyl-benzofuran-5-yl)-methanol

HRID 1827977Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1827977
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:10][C:9]=2[CH:19]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.CCOCC.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>[C:13]1([C:11]2[O:12][C:8]3[CH:7]=[CH:6][C:5]([CH2:3][OH:2])=[CH:19][C:9]=3[CH:10]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

6

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 66865443Methyl 2-phenylbenzofuran-5-carboxylate

Produkt 1

HCID 22062820(2-Phenyl-benzofuran-5-yl)-methanolAusbeute 87,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 62649Sodium sulfate decahydrateLösungsmittel

Versuchsvorschrift

To a solution of 2-phenyl-benzofuran-5-carboxylic acid methyl ester 27 (0.7 g, 2.8 mmol) in THF (15 ml) was added dropwise a solution of lithium aluminum hydride (1M in THF) (3.6 ml, 3.6 mmol) at 0° C. After the addition, the reaction mixture was allowed to warm to room temperature and stirred for 2 hrs. The mixture was cooled to 0° C., diluted with ether and sodium sulfate decahydrate was added. After filtration the solids were washed with ether, and the organic layer was washed and dried. Evaporation of the solvent and purification by chromatography yielded (2-phenyl-benzofuran-5-yl)-methanol (0.55 g). A mixture of (2-phenyl-benzofuran-5-yl)-methanol (0.5 g, 2.23 mmol), (R)-2-isocyanato-3-phenyl-propionic acid methyl ester 5 (0.55 g, 2.68 mmol), triethylamine (0.74 ml, 5.35 mmol) and THF (15 ml) was heated at 50° C. for 6 hrs. Additional (R) 2-isocyanato-3-phenyl-propionic acid methyl ester 5 (0.15 g) was added, and the mixture was stirred at 50° C. overnight. The solvent was evaporated and the residue was partitioned between ethyl acetate and water. After extraction and evaporation of the solvent, the residue was purified by chromatography to give about 0.76 g of (R)-3-phenyl-2-(2-phenyl-benzofuran-5-ylmethoxycarbonylamino)-propionic acid methyl ester 28.

Aufarbeitung

  1. additionAfter the addition
  2. temperatureThe mixture was cooled to 0° C.
  3. additionwas added
  4. filtrationAfter filtration the solids
  5. washwere washed with ether
  6. washthe organic layer was washed
  7. customdried
  8. customEvaporation of the solvent and purification by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-353dc66a23aa424a852b2277388a2327
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07056903B2

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