HCID 90031358, compound → HCID 90057790, compound
Reaction equation
[CH2:1]([C:4]1[CH:11]=[C:10]([F:12])[CH:9]=[C:6]([CH:7]=[O:8])[C:5]=1[OH:13])[CH:2]=[CH2:3]>C1(SC2C=CC=CC=2)C=CC=CC=1.CCOC(C)=O>[F:12][C:10]1[CH:11]=[C:4]([CH2:1][CH2:2][CH3:3])[C:5]([OH:13])=[C:6]([CH:9]=1)[CH:7]=[O:8]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a round-bottom flask were added aldehyde 47d (1.10 g, 6.11 mmol, 1.0 equiv.), 5% Pd/C (220 mg, 20 wt % of 47d), diphenyl sulfide (10 μL, 0.061 mmol, 0.010 equiv.), and EtOAc (25 mL, 0.25 M). The reaction mixture was stirred overnight at room temperature under an atmosphere of H2 (balloon pressure). The reaction mixture was filtered through Celite and washed thoroughly with EtOAc. The filtrate was concentrated to afford aldehyde 47e (991 mg, 89.3%) as a yellow oil. 1H-NMR (500 MHz, CDCl3) δ 11.06 (br s, 1H), 9.80 (s, 1H), 7.12 (dd, 1H, J=3.0, 9.0 Hz), 7.06 (dd, 1H, J=3.0, 7.5 Hz), 2.62 (t, 2H, J=7.5 Hz), 1.63 (sext, 2H, J=7.5 Hz), 0.96 (t, 3H, J=7.5 Hz). 13C-NMR (125 MHz, CDCl3) δ 195.9 (d, JC-F=2.5 Hz), 156.3 (d, JC-F=1.0 Hz), 155.5 (d, JC-F=238.1 Hz), 133.9 (d, JC-F=6.3 Hz), 124.7 (d, JC-F=23.1 Hz), 119.6 (d, JC-F=6.5 Hz), 115.4 (d, JC-F=22.4 Hz), 31.2, 22.4, 14.0. 19F-NMR (470 MHz, CDCl3) δ −127.3. HRMS (EI): 182.07392 (M+); calcd. for C10H11FO2: 182.07431.