[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:17])[C:11]#[C:12][Si:13]([CH3:16])([CH3:15])[CH3:14])([O-])=O.Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:17])[CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14]To the solution of 1-(2-nitrophenyl)-3-(trimethylsilyl)prop-2-yn-1-one (11) (294 g; 1.19 mole) in toluene (4.5 L) was added Pd/C (10% wt; 30 g) under N2. The resulting suspension was degassed under vacuum and back-filled 3-times with H2. The mixture was hydrogenated under 0.3 MPa of hydrogen at room temperature for 72 hours. The progress of the reaction was monitored by HPLC. When the HPLC analysis indicated the disappearance of compound (II), the catalyst was filtered off through a Celite pad. The filtrate was concentrated under vacuum to give the crude product as black liquid. HPLC analysis showed 90% purity. The crude product was dissolved in ethyl acetate (7.5 L) and treated with 4N hydrochloric acid (600 mL). After the phase separation, HPLC analysis showed the 92.8% purity. The organic phase was washed again with 4 N hydrochloric acid (600 mL). The organic phase was further washed with 4 N hydrochloric acid (500 mL) one additional time. The organic phase was dried over sodium sulfate (200 g), concentrated to give the crude product (3) (220 g; 84% yield).
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