反应详情

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.

1. filtrationThe mixture is filtered through a pad of Celite®
2. concentrationconcentrated in vacuo
3. dissolutionThe residue is dissolved in toluene (30 mL)
4. additiontreated with p-tolunesulfonic acid (0.1 g)
5. temperaturerefluxed for 2 h
6. concentrationconcentrated in vacuo
7. customThe residue is chromatographed on SiO2 (10% ethyl acetate/hexanes