HCID 69365855, Verbindung → 4-(2-Phenylethyl)oxolan-2-one
Reaktionsgleichung
CO[C:3](=[O:23])[CH:4]=[C:5]([CH2:14][O:15]CC1C=CC=CC=1)[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>[Pd].C(O)(=O)C>[CH2:6]([CH:5]1[CH2:14][O:15][C:3](=[O:23])[CH2:4]1)[CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A mixture of 3-benzyloxymethyl-5-phenyl-pent-2-enoic acid methyl ester, (3.2 g, 13.5 mmol), 10 wt. % palladium on activated carbon (3.2 g), and acetic acid (40 mL) is placed in a Parr® Shaker under hydrogen (45 PSI) and shaken 4 h. The mixture is filtered through a pad of Celite® and concentrated in vacuo. The residue is dissolved in toluene (30 mL), treated with p-tolunesulfonic acid (0.1 g), refluxed for 2 h and concentrated in vacuo. The residue is chromatographed on SiO2 (10% ethyl acetate/hexanes then 50% ethyl acetate/hexanes) to yield the title compound 1.2 g (62%) as a colorless liquid.