{4-[2-(4-Benzyloxy-phenyl)-ethyl]-2-methyl-4,5-dihydro-oxazol-4-yl}-methanol → 4-[2-(4-Hydroxymethyl-2-methyl-4,5-dihydro-oxazol-4-yl)-ethyl]-phenol

HRID 600197

Reaktionsgleichung

Reaktionsgleichung von HRID 600197
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]2([CH2:23][OH:24])[CH2:21][O:20][C:19]([CH3:22])=[N:18]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[OH:24][CH2:23][C:17]1([CH2:16][CH2:15][C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)[CH2:21][O:20][C:19]([CH3:22])=[N:18]1

Komponenten

4

Edukt 1

HCID 67054626{4-[2-(4-Benzyloxy-phenyl)-ethyl]-2-methyl-4,5-dihydro-oxazol-4-yl}-methanol

Produkt 1

HCID 579352584-[2-(4-Hydroxymethyl-2-methyl-4,5-dihydro-oxazol-4-yl)-ethyl]-phenol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of {4-[2-(4-benzyloxy-phenyl)-ethyl]-2-methyl-4,5-dihydro-oxazol-4-yl}-methanol (26.1 g, 0.08 mol) in methanol (800 ml) is added palladium on charcoal (2.6 g, 10% wt), and the reaction mixture is stirred under hydrogen atmosphere at RT for 5 hours. The reaction mixture is then filtered through celite and concentrated under vacuum. (R/S)-4-[2-(4-Hydroxymethyl-2-methyl-4,5-dihydro-oxazol-4-yl)-ethyl]-phenol is isolated in quantitative yield after crystallization with ethyl acetate and hexanes.

Aufarbeitung

  1. filtrationThe reaction mixture is then filtered through celite
  2. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-232eea4456b04c4d9686b4294fccd46d
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902175B2

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