Ethyl benzoylacetate → Ethyl 3-phenylhydracrylate, (+-)-

참여 물질

반응 단계

Ethyl benzoylacetate (1) (19.21 g; 0.10 mol) was dissolved in 95% ethanol (100 mL) in a pressure bottle. The bottle was purged with nitrogen and 5% palladium on carbon (960 mg; 5 weight %) was added. The vessel was placed under 45 psi H2 and shaken on a Parr apparatus for 14 hours, at which time H2 uptake had halted and thin layer chromatographic analysis indicated (1) was present. The reaction mixture was suction-filtered through Celite with a top sand layer (to prevent channels) and eluted with ether to remove the catalyst. The filtrate was concentrated to afford (2), racemic ethyl 3-phenyl-3-hydroxypropionate (19.17 g; 99%) which was pure by tlc and 1H nmr analysis. 1H nmr (300 MHz, CDCl3): 7.4-7.2 (5H, m); 5.130(1H,dd,J=4.36, 8.48 Hz); 4.178 (2H, q, J=7.17 Hz); 3.2(1H, br s); 2 764(1H, dd, J=8.58, 16.30 Hz); 2.691 (1H, dd, J=4.33, 16.33 Hz); 1.259(3H, t, J=7.17 Hz). IR (neat film, cm-1) 3450 (s,b); 1720(s); 1605(w). EIMS (m/e): 194 (M+); 165 (2%, M+ - Et); 149 (5%, M+ -EtO).

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