E-{5-Fluoro-2-[2-(4-methoxyphenyl)vinyl]phenyl}methanol → {5-Fluoro-2-[2-(4-methoxyphenyl)ethyl]phenyl}methanol

HRID 1927413Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1927413
[F:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[C:6]([CH2:8][OH:9])[CH:7]=1>[Pd].CO.C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)=[C:6]([CH2:8][OH:9])[CH:7]=1

Komponenten

5

Edukt 1

HCID 57831377E-{5-Fluoro-2-[2-(4-methoxyphenyl)vinyl]phenyl}methanol

Produkt 1

HCID 57831395{5-Fluoro-2-[2-(4-methoxyphenyl)ethyl]phenyl}methanol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 6.8 g (26.33 mmol) of E-{5-fluoro-2-[2-(4-methoxyphenyl)vinyl]phenyl}methanol and 0.5 g of 10% palladium on carbon in 50 ml of methanol and 250 ml of ethanol is hydrogenated under atmospheric pressure at room temperature for 1 hour. After reaction has stopped, the mixture is filtered through kieselguhr and the filtrate is then concentrated to dryness. The resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1→4:1→1:1). 5.95 g (87% of theory) of a colorless solid are obtained.

Aufarbeitung

  1. customAfter reaction
  2. filtrationthe mixture is filtered through kieselguhr
  3. concentrationthe filtrate is then concentrated to dryness
  4. customThe resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1→4:1→1:1)
  5. custom5.95 g (87% of theory) of a colorless solid are obtained

Quellen und Nachweise

ORD-Eintrag
ord-0f38cdec21d3467f99f806c49c824060
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183271B2

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