Sodium Hydroxide → [2-Methyl-5-(4-trifluoromethyl-phenyl)-furan-3-yl]-methanol

HRID 9635Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 9635
[CH3:1][C:2]1[O:3][C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[CH:5][C:6]=1[C:7](OC)=[O:8].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1.CCOCC.O>[CH3:1][C:2]1[O:3][C:4]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:19])([F:18])[F:20])=[CH:15][CH:16]=2)=[CH:5][C:6]=1[CH2:7][OH:8]

Komponenten

7

Edukt 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21986466Methyl 2-methyl-5-[4-(trifluoromethyl)phenyl]-3-furoate2×

Produkt 1

HCID 21986436[2-Methyl-5-(4-trifluoromethyl-phenyl)-furan-3-yl]-methanol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of methyl 2-methyl-5-[4-(trifluoromethyl)phenyl]-3-furoate (intermediate 23, 0.27 g) in tetrahydrofuran (10 ml) stirred at 0° C. under a nitrogen atmosphere was treated with 1M lithium aluminium hydride in ether (1.0 ml). The reaction mixture was stirred at this temperature for 4 hours and then water (2 ml) and 2M aqueous sodium hydroxide (2 ml) added. The reaction mixture was further diluted with water; extracted with ethyl acetate and the organic solution extracted with water and dried with brine and over sodium sulfate and concentrated. The product isolated after evaporation of the solvent was further purified by Biotage™ chromatography using a mixture of petroleum ether:ethyl acetate (1:1) as eluent to give the title compound as a white solid.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. extractionthe organic solution extracted with water
  3. dry with materialdried with brine and over sodium sulfate
  4. concentrationconcentrated
  5. customThe product isolated
  6. customafter evaporation of the solvent
  7. customwas further purified by Biotage™ chromatography
  8. additiona mixture of petroleum ether:ethyl acetate (1:1) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-55af0c1fec17466ca50bb1b0a293d948
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091237B2

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